Triethylamine → Z-Gly-Gly-OtBu

HRID 2258325Notes

Reaction equation

HRID 2258325 reaction equation
[C:1]([NH:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:16]([O:20][C:21](=[O:24])[CH2:22][NH2:23])([CH3:19])([CH3:18])[CH3:17].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C>[C:16]([O:20][C:21](=[O:24])[CH2:22][NH:23][C:13](=[O:15])[CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14349BenzyloxycarbonylglycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 151417Glycine tert-butyl ester

Product 1

HCID 15403804Z-Gly-Gly-OtBuYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Carbobenzyloxy-glycine (2.1 g, 10 mmol) and glycine-tert-butyl ester (1.3 g, 10 mmol) were coupled using benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (4.4 g, 10 mmol) and triethylamine (1.5 g, 15 mmol) in acetonitrile following the method described in Example 23 to give 2.5 g(79%) of N-carbobenzyloxy-glycylglycine-tert-butyl ester after chromatography on silica gel.

Sources & evidence

ORD record
ord-4c06431601584ab6b5d606d982c995da
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

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