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

HRID 267130Notes

Reaction equation

HRID 267130 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-e405b78588e84f0cbef8f4d84de018f0
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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