Hydrogen Bromide → 2'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

HRID 1979255Notes

Reaction equation

HRID 1979255 reaction equation
C(OC(C([C@@H:17]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:18]([NH:20][N:21]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:22](=[O:43])[C@@H:23]([CH3:42])[NH:24][C:25]([O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])=[O:19])C/C=C/C1SC=CC=1)=O)(C)(C)C.Br>ClCCl.C(O)(=O)C>[CH2:44]([N:21]([C:22](=[O:43])[C@@H:23]([CH3:42])[NH:24][C:25]([O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[NH:20][C:18](=[O:19])[CH2:17][CH2:48][CH:49]([CH3:51])[CH3:50])[CH:45]([CH3:46])[CH3:47]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 131722591(E)-2(R)-[1(RS)-[(tert.butyloxy)carbonyl]-4-(2-thienyl)-3-butenyl]-2'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

Product 1

HCID 1317225872'-isobutyl-2'-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.04 g of (E)-2(R)-[1(RS)-[(tert.butyloxy)carbonyl]-4-(2-thienyl)-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in 50 ml of dichloromethane was treated with 1.0 ml of a 33% solution of hydrogen bromide in acetic acid at −15° C. The mixture was stirred at this temperature for 1.5 hours and then washed with water and dried over anhydrous magnesium sulfate. Evaporation was followed by addition of hexane and filtration of the resulting precipitate. The precipitate was dried to give 0.665 g of (E)-2(R)-[1(RS)-(carboxy)]-4-(2-thienyl)-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethyloxycarbonyl)-D-alanyl]-4-methylvalerohydrazide in the form of a light brown solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation
  4. additionwas followed by addition of hexane and filtration of the resulting precipitate
  5. customThe precipitate was dried

Sources & evidence

ORD record
ord-f2c2404e052446529186e3842641a216
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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