Trifluoroacetic acid → HCID 86756894, compound

HRID 1979202Notes

Reaction equation

HRID 1979202 reaction equation
C([O:5][C:6]([C@H:8]([C@@H:18]([CH2:54][CH:55]([CH3:57])[CH3:56])[C:19]([NH:21][N:22]([CH2:50][CH:51]([CH3:53])[CH3:52])[C:23](=[O:49])[C@@H:24]([CH2:43][O:44]C(C)(C)C)[NH:25][C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([C@H:8]([C@@H:18]([CH2:54][CH:55]([CH3:57])[CH3:56])[C:19]([NH:21][N:22]([CH2:50][CH:51]([CH3:52])[CH3:53])[C:23](=[O:49])[C@@H:24]([CH2:43][OH:44])[NH:25][C:26]([O:28][CH2:29][CH:30]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=2[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:27])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86756895HCID 86756895, compound

Product 1

HCID 86756894HCID 86756894, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.05 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethyloxycarbonyl)-O-tert.butyl-D-seryl]-4-methylvalerohydrazide in 5 ml of dichloromethane was treated at room temperature under nitrogen with 5 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2.5 hours and evaporated. Final traces of trifluoroacetic acid were removed by the addition and evaporation of three 10 ml portions of toluene. The residue in diethyl ether was treated with hexane to yield 0.78 g of (E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-2′-isobutyl-2′[N-(9-fluorenylmethyloxycarbonyl)-D-seryl]-4-methylvalerohydrazide as a white solid.

Workup

  1. customevaporated
  2. customwere removed by the addition and evaporation of three 10 ml portions of toluene
  3. additionThe residue in diethyl ether was treated with hexane

Sources & evidence

ORD record
ord-21d93f8d9c1b4b8b832dcae2926bb2ca
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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