Diazomethane → benzyl [2-(4-methoxyphenyl)-l(S)-(2-diazoacetyl)ethyl]carbamate

HRID 54071Notes

Reaction equation

HRID 54071 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.[N+:33](=[CH2:35])=[N-:34]>>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:22](=[O:24])[CH:35]=[N+:33]=[N-:34])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 53748252benzyl [2-(4-methoxyphenyl)-l(S)-(2-diazoacetyl)ethyl]carbamate

Procedure

In a manner analogous to that described in Example 19(i), 3.10 g of N-(benzyloxycarbonyl)-3-(4-methoxyphenyl)-L-alanine were treated with isobutyl chloroformate followed by diazomethane to give 2.83 g of benzyl [2-(4-methoxyphenyl)-1(S)-(2-diazoacetyl)ethyl]carbamate as a pale yellow solid of melting point 88°-90° C.

Sources & evidence

ORD record
ord-35f49ed163ac44408ab12a6e1f96695d
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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