Triethylamine → 2-(N-benzyloxycarbonyl-DL-methionylamino)-1,3,4-thiadiazole

HRID 850954Notes

Reaction equation

HRID 850954 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]([OH:19])=O)[CH2:13][CH2:14][S:15][CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:33][C:34]1[S:35][CH:36]=[N:37][N:38]=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]([NH:33][C:34]1[S:35][CH:36]=[N:37][N:38]=1)=[O:19])[CH2:13][CH2:14][S:15][CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 199091,3,4-Thiadiazol-2-amineHCID 97806N-benzyloxycarbonyl-DL-methionine

Product 1

HCID 131455142-(N-benzyloxycarbonyl-DL-methionylamino)-1,3,4-thiadiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9.5 g of N-benzyloxycarbonyl-DL-methionine, 3.4 g of triethylamine, 150 ml of chloroform, 3.7 g of ethyl chlorocarbonate and 3.4 g of 2-amino-1,3,4-thiadiazole were reacted in the same manner as in Example 1(i) to obtain 10.3 g (yield: 84%) of 2-(N-benzyloxycarbonyl-DL-methionylamino)-1,3,4-thiadiazole as white crystals having a melting point of 155°-159° C.

Sources & evidence

ORD record
ord-bd6b1cc67e5d4c899c5ff036664d22ab
Source dataset
uspto-grants-1983_05
Patent number
US04382142

Reaction notes

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