Diazomethane → benzyl [2-(4-tert.butoxyphenyl)-1(S)-(2-diazoacetyl)ethyl]carbamate

HRID 267119Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25](O)=[O:26])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCC(F)(F)C(O)CC[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)C[C@H]1O.C1CCC(NC2CCCCC2)CC1.ClC(OCC(C)C)=O.[N+:76](=[CH2:78])=[N-:77]>>[C: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:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:25](=[O:26])[CH:78]=[N+:76]=[N-:77])=[CH:19][CH:18]=1)([CH3:22])([CH3:23])[CH3:24]

Participants

Reactant 4

HCID 9550Diazomethane

HCID 62365Isobutyl chloroformate

HCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosine

HCID 7174909515-Hydroxy Lubiprostone Dicyclohexylammonium Salt

Product 1

HCID 57129157benzyl [2-(4-tert.butoxyphenyl)-1(S)-(2-diazoacetyl)ethyl]carbamate

Procedure

In a manner analogous to that described in Example 19(i), N-(benzyloxycarbonyl)-3-(4-tert.butoxyphenyl)-L-alanine (prepared from 7.45 g of the dicyclohexylammonium salt) was treated with isobutyl chloroformate followed by reaction with diazomethane to give 3.58 g of benzyl [2-(4-tert.butoxyphenyl)-1(S)-(2-diazoacetyl)ethyl]carbamate as a yellow solid of melting point 80°-82° C.

Sources & evidence

ORD record: ord-9339ffc212e64f3d8bc260d7ca76d8bb
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652369

Reaction notes

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