Benzyl succinimido carbonate → Methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

HRID 854279Notes

Reaction equation

HRID 854279 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH3:19])[CH2:11][NH:12][C@@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](ON1C(=O)CCC1=O)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>ClCCl>[CH2:23]([O:22][C:20]([N:12]([CH2:11][CH:10]([CH3:19])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 86607768methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Product 1

HCID 69154997Methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate (2.5 g, −8.9 mmol) in dichloromethane (50 mL) was added Cbz-OSu (2.25 g, 9.0 mmol). The resulting mixture was stirred at room temperature for 3 days. The solvent was removed on a rotavap, and the crude product was purified by flash chromatography on a Biotage® system (silica, 25-80% ethyl acetate in hexanes) to yield methyl N-[(benzyloxy)carbonyl]-N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate as colorless viscous oil. MS (M+1−Boc): 309.4

Workup

  1. customThe solvent was removed on a rotavap
  2. customthe crude product was purified by flash chromatography on a Biotage® system (silica, 25-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-98894a7a229042e686c91ddd17331d03
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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