1-Hydroxybenzotriazole → Boc-Thz-Gly-NH2

HRID 2269653Notes

Reaction equation

HRID 2269653 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH2:5])=[O:4].[N:13]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][S:19][CH2:18][C@H:14]1[C:15]([OH:17])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl.C(N(CC)CC)C>[N:13]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][S:19][CH2:18][C@H:14]1[C:15]([NH:1][CH2:2][C:3]([NH2:5])=[O:4])=[O:17]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

Product 1

HCID 130288245Boc-Thz-Gly-NH2Yield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Deprotection of 500 mg of Boc-Gly-NH2 was performed similarly to that in Example 28 (Process 3), and the obtained product was dissolved in dichloromethane, and 0.39 ml of tri-ethylamine, 0.67 g of Boc-Thz-OH, 0.47 g of HOBt and 0.64 g of EDC hydrochloride were added under ice cooling and the mixture was stirred overnight at room temperature. The reaction mixture was treated similarly to that in Example 139 (Process 2) to give 0.54 g of the title compound as oil.

Workup

  1. additionThe reaction mixture was treated similarly to that in Example 139 (Process 2)

Sources & evidence

ORD record
ord-ac67db8da1bf49a8aa164b93080aa93f
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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