Trifluoroacetic acid → HCID 68114567, compound

HRID 1200140Notes

Reaction equation

HRID 1200140 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]([NH:17][C:18](=[O:37])[C@@H:19]([NH:29]C(OC(C)(C)C)=O)[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.C1(OC)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:16][C:9]([NH:17][C:18](=[O:37])[C@@H:19]([NH2:29])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:8])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14696294HCID 14696294, compound

Product 1

HCID 68114567HCID 68114567, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

15.09 g of trifluoroacetic acid were added to a solution of 9.0 g of (2S)-N-(α,α-dimethylbenzyl)-3-benzyloxy-2-(t-butoxycarbonylamino)propionamide (prepared as described in Preparation 4) in a mixture of 100 ml of methylene chloride and 2.4 g of anisole, and the whole mixture was stirred for 1 hour at room temperature. At the end of this time, the excess trifluoroacetic acid was distilled off. On adding diethyl ether, the residue gave 8.8 g of the title compound as needles melting at 148°-150° C.

Workup

  1. distillationAt the end of this time, the excess trifluoroacetic acid was distilled off
  2. additionOn adding diethyl ether

Sources & evidence

ORD record
ord-16e3051db0be473d8a04b06905d02700
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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