N-(tert-butoxycarbonyl)glycine → HCID 89845514, compound

HRID 334002Notes

Reaction equation

HRID 334002 reaction equation
[ClH:1].Cl.[CH2:3]([NH:11][CH2:12][C@H:13]([NH:15][S:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2)(=[O:18])=[O:17])[CH3:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(OC([NH:36][CH2:37][C:38](O)=[O:39])=O)(C)(C)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[ClH:1].[NH2:36][CH2:37][C:38]([N:11]([CH2:12][C@H:13]([NH:15][S:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2)(=[O:18])=[O:17])[CH3:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:39]

Participants

5

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57389812HCID 57389812, compound

Product 1

HCID 89845514HCID 89845514, compoundYield 151.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A free form (220 mg) of the compound of Example 23 and N-(tert-butoxycarbonyl)glycine (25 mg) were condensed (230 mg, 73%) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (137 mg) in dichloromethane. Subsequently, 100 mg of the title compound was obtained as a white solid (61%) from 150 mg of a free form according to the methods described in Steps 2 and 3 of Example 1.

Workup

  1. customcondensed (230 mg, 73%)

Sources & evidence

ORD record
ord-a2e9b0bdefac4344bbad8c13498398f0
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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