Hydrogen Bromide → 3-[3 (S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide

HRID 466859Notes

Reaction equation

HRID 466859 reaction equation
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:21]([OH:35])[CH2:22][N:23]1[C@H:27]([C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][S:25][CH2:24]1)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15])=O)C1C=CC=CC=1.Br>C(O)(=O)C.C(OCC)C>[NH2:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:21]([OH:35])[CH2:22][N:23]1[C@H:27]([C:28]([NH:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:26][S:25][CH2:24]1)=[O:18])[CH2:13][C:14](=[O:16])[NH2:15]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 4735922-{[(Benzyloxy)(hydroxy)methylidene]amino}-N~1~-(4-{4-[(tert-butylimino)(hydroxy)methyl]-1,3-thiazolidin-3-yl}-3-hydroxy-1-phenylbutan-2-yl)butanediimidic acid

Product 1

HCID 700409433-[3 (S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 170 mg of 3-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide and 0.3 ml of 32% (w/w) hydrogen bromide in glacial acetic acid was stirred at room temperature for 1 hour. The solution was diluted with diethyl ether and the precipitated solid was rapidly filtered off, washed with diethyl ether and dissolved in water. The solution was made alkaline by the addition of potassium carbonate and extracted with three portions of chloroform. The combined chloroform extracts were dried over anhydrous sodium sulphate, filtered and evaporated to give 110 mg of 3-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide; MS: m/e 466 [M+H]+.

Workup

  1. filtrationthe precipitated solid was rapidly filtered off
  2. washwashed with diethyl ether
  3. dissolutiondissolved in water
  4. additionby the addition of potassium carbonate
  5. extractionextracted with three portions of chloroform
  6. dry with materialThe combined chloroform extracts were dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-77c51421e7414c588ccba331568c2a74
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

Loading…