Ethyl chloroformate → HCID 53632373, compound

HRID 2253944Notes

Reaction equation

HRID 2253944 reaction equation
[C:1]([C:3](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=1)[C:4]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]N=1)=[O:5])#[N:2].C(C(=CC1C=CC(O)=C(O)C=1)[C:27]([O:29][CH2:30][CH2:31]CCCCCCN1C=CN=C1)=[O:28])#N.C(C(=CC1C=CC(O)=C(O)C=1)[C:55]([O:57][CH2:58][CH2:59]C1C=CC(N)=CC=1)=[O:56])#N.[C:76]([C:78](=CC1C=CC(O)=C(O)C=1)C(OCCOC1C=CC=CC=1)=O)#N.C(C(=CC1C=CC(O)=C(O)C=1)C(OCC=CC1C=CC=CC=1)=O)#N.ClC(OCC)=O.C(C(=CC1C=CC(OC(OCC)=O)=C(OC(OCC)=O)C=1)C(OCCC1C=CC=CN=1)=O)#N.C(C(=CC1C=CC(O)=C(OC(OCC)=O)C=1)C(OCCCCCCCCN1C=CN=C1)=O)#N.C(C(=CC1C=CC(OC(OCC)=O)=C(OC(OCC)=O)C=1)C(OCCC1C=CC(N)=CC=1)=O)#N.C(C(=CC1C=CC(OC(OCC)=O)=C(OC(OCC)=O)C=1)C(OCCOC1C=CC=CC=1)=O)#N>>[C:1]([C:3](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:55]([O:57][CH2:58][CH3:59])=[O:56])=[C:18]([O:23][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:17]=1)[C:4]([O:6][CH2:7][CH:8]=[CH:9][C:14]1[CH:78]=[CH:76][CH:11]=[CH:12][CH:13]=1)=[O:5])#[N:2]

Participants

11

Reactant 10

HCID 10928Ethyl chloroformateHCID 6610363HCID 6610363, compoundHCID 53903019HCID 53903019, compoundHCID 53971961HCID 53971961, compound2×HCID 53989437HCID 53989437, compoundHCID 54122616HCID 54122616, compound2×HCID 54176288HCID 54176288, compound2×HCID 54262434HCID 54262434, compoundHCID 54358728HCID 54358728, compound2×HCID 54410201HCID 54410201, compound

Product 1

HCID 53632373HCID 53632373, compound

Procedure

By using 2-pyridylethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate, 8-(imidazol-1-yl)-octanyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate, 4-amino-phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate, phenoxyethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate and cinnamyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate instead of phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate and 2.0-2.2 equivalents of ethyl chloroformate as an alkyl chloroformate and reacting them in a similar manner to the process of Example 1, 2-pyridylethyl 2-cyano-3-(3,4-diethoxycarbonyloxyphenyl)-2-propenoate (Compound 24), 8-(imidazol-1-yl)-octanyl 2-cyano-3-(3-ethoxycarbonyloxy-4-hydroxyphenyl)-2-propenoate (Compound 25), 4-aminophenethyl 2-cyano-3-(3,4-diethoxycarbonyloxyphenyl)-2-propenoate (Compound 26), phenoxyethyl 2-cyano-3-(3,4-diethoxycarbonyloxyphenyl)-2-propenoate (Compound 27) and cinnamyl 2-cyano-3-(3,4-diethoxycarbonyloxyphenyl)-2-propenoate (Compound 28) were obtained, respectively.

Sources & evidence

ORD record
ord-568382a4f23443ec86fb643686436385
Source dataset
uspto-grants-1993_08
Patent number
US05232941

Reaction notes

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