Trifluoroacetic acid → HCID 23387524, compound

HRID 1170621Notes

Reaction equation

HRID 1170621 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 modified as described below.

Workup

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

Sources & evidence

ORD record
ord-083dc4607d454e848e0120d715c0f981
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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