Trifluoroacetic acid → HCID 23387524, compound

HRID 989964Notes

Reaction equation

HRID 989964 reaction equation
COC1C=CC(C[CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:36])[C@H:21]([CH:33]([CH3:35])[CH3:34])[NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:15]([O:37][C:38](=[O:54])[C@H:39]([CH:51]([CH3:53])[CH3:52])[NH:40][C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[O:42])[CH:14]=2)[C:9]([O-:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[C:41]([NH:40][C@H:39]([C:38]([O:37][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][C:20](=[O:36])[C@H:21]([CH:33]([CH3:35])[CH3:34])[NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH2:12][CH2:8][C:9]([OH:11])=[O:10])=[O:54])[CH:51]([CH3:52])[CH3:53])([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86585846HCID 86585846, compound

Product 1

HCID 23387524HCID 23387524, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzyl-3,4-di-(N-CBZ-L-valyloxy)hydrocinnamate (10 g, 13 mmol) was dissolved in dichloromethane and 1,1,1 trifluoroacetic acid (30 ml) and left at ambient temperature for 3.5 h. Evaporation under reduced pressure and purification by chromatography (chloroform-methanol, 10:1) yielded 6.7 g (80%) pure title product. The compound can be activated and esterified to a drug or further modifiedas described below.

Workup

  1. customEvaporation
  2. customunder reduced pressure and purification by chromatography (chloroform-methanol, 10:1)

Sources & evidence

ORD record
ord-8eef3ab7a6ec4f13900c18960d57f371
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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