Hydrogen Bromide → H-Thz-NH-tBu

HRID 267127Notes

Reaction equation

HRID 267127 reaction equation
C(OC([N:11]1[C@H:15]([C:16]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][S:13][CH2:12]1)=O)C1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[C:19]([NH:18][C:16]([C@@H:15]1[CH2:14][S:13][CH2:12][NH:11]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 186482733-(benzyloxycarbonyl)-N-tert.butyl-4(R)-thiazolidinecarboxamide

Product 1

HCID 10535636H-Thz-NH-tBuYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.2 g of 3-(benzyloxycarbonyl)-N-tert.butyl-4(R)-thiazolidinecarboxamide and 10 ml of 32% (w/w) hydrogen bromide in glacial acetic acid was stirred at room temperature for 2 hours. The resulting solution was poured into diethyl ether and the precipitated hydrobromide salt of the product was filtered off, washed with diethyl ether and then dissolved in water. The solution was made alkaline by the addition of 1M sodium hydroxide solution and extracted twice with dichloromethane. The combined dichloromethane extracts were washed with water, dried over anhydrous sodium sulphate, filtered and evaporated to give 1.57 g of N-tert.butyl-4(R)-thiazolidinecarboxamide as a crystalline solid of melting point 68°-71° C.

Workup

  1. filtrationthe precipitated hydrobromide salt of the product was filtered off
  2. washwashed with diethyl ether
  3. dissolutiondissolved in water
  4. additionby the addition of 1M sodium hydroxide solution
  5. extractionextracted twice with dichloromethane
  6. washThe combined dichloromethane extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-5133d5fe021644478fd981c650250d4e
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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