Triethylamine → HCID 13037997, compound

HRID 850958Notes

Reaction equation

HRID 850958 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:36][C:37]1[S:38][CH:39]=[N:40][N:41]=1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([NH:36][C:37]1[S:38][CH:39]=[N:40][N:41]=1)=[O:22])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 199091,3,4-Thiadiazol-2-amineHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 13037997HCID 13037997, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the same procedure as in Example 1(i), 10 g of N-t-butoxycarbonyl-L-tryptophan, 3.3 g of triethylamine, 3.5 g of ethyl chlorocarbonate and 3.3 g of 2-amino-1,3,4-thiadiazole were reacted in 150 ml of chloroform to obtain 10.7 g (yield: 84%) of 2-(N-t-butoxycarbonyl-L-tryptophanylamino)-1,3,4-thiadiazole as light yellow powder of mp: 98°-101° C. (dec.) and [α]D20 : +41.0° (C=1.0, MeOH).

Sources & evidence

ORD record
ord-96df05a81afe40e2bd88e24947428a3e
Source dataset
uspto-grants-1983_05
Patent number
US04382142

Reaction notes

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