Dimethylformamide → HCID 31934446, compound

HRID 427362Notes

Reaction equation

HRID 427362 reaction equation
CN(C=O)C.[NH:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:7]([C:15]([OH:17])=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC(C)C)=O.[CH2:33]([NH2:37])[CH:34]([CH3:36])[CH3:35]>C(N(CC)CC)C>[NH:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:7]([C:15]([NH:37][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6558IsobutylamineHCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 31934446HCID 31934446, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a DMF solution containing a mixed anhydride prepared from 2.0 g oi Boc-Phe-OH, 1.15 ml of triethylamine and 1.08 ml of isobutyl chloroformate, 1.50 ml of isobutylamine was added under ice cooling and the resultant mixture was stirred for 14 hr. The reaction mixture was treated similarly to that in Example 51 (Process 1) to give 1.91 g of the title compound.

Workup

  1. additionwas added under ice cooling
  2. additionThe reaction mixture was treated similarly to that in Example 51 (Process 1)

Sources & evidence

ORD record
ord-cc99ccb118ef4c98a3ad54a3d1f97cdf
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

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