2,5-dioxopyrrolidin-1-yl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

• ChemBase ID: 152198
• Molecular Formular: C20H23N3O6
• Molecular Mass: 401.41312
• Monoisotopic Mass: 401.15868547
• SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H](C(=O)ON1C(=O)CCC1=O)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C20H23N3O6/c1-20(2,3)28-19(27)22-15(18(26)29-23-16(24)8-9-17(23)25)10-12-11-21-14-7-5-4-6-13(12)14/h4-7,11,15,21H,8-10H2,1-3H3,(H,22,27)/t15-/m0/s1
• InChIKey: CPJXMXQYRHNIFU-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoate
• Synonyms: Nα-Boc-L-tryptophan hydroxysuccinimide ester; Boc-Trp-OSu; Boc-Trp-OSu; Nα-Boc-L-色氨酸羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 3392-11-8
• EC Number: 222-234-4
• MDL Number: MFCD00022756
• Beilstein Number: 462939
• PubChem SID: 24849490; 162246343
• PubChem CID: 98767

CALCULATED PROPERTIES

• Acid pKa: 13.26109
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.0380597
• LogD (pH = 7.4): 2.0380592
• Log P: 2.0380597
• Molar Refractivity: 101.6296 cm^3
• Polarizability: 40.893143 Å^3
• Polar Surface Area: 117.8 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 146-148 °C
• Optical Rotation: [α]20/D -23.5±1.0°, c = 1% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 95+%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C20H23N3O6

DETAILS

Sigma Aldrich - 15516

Packaging
5 g in glass bottle