Butyl chloroformate → Methyl 4-[6-(butoxycarbonyl)amino-2,3,5-trimethylindol-1-ylmethyl]-3-methoxybenzoate

HRID 358739Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:25])=[C:7]([CH3:24])[N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][C:3]=1[CH3:26].Cl[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29]>>[CH2:31]([O:30][C:28]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:25])=[C:7]([CH3:24])[N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][C:3]=1[CH3:26])=[O:29])[CH2:32][CH2:33][CH3:34]

Participants

Reactant 2

HCID 61140Butyl chloroformate

HCID 19744303Methyl 4-(6-amino-2,3,5-trimethylindol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 53990328Methyl 4-[6-(butoxycarbonyl)amino-2,3,5-trimethylindol-1-ylmethyl]-3-methoxybenzoateYield 99%

Procedure

Similarly, starting from methyl 4-(6-amino-2,3,5-trimethylindol-1-ylmethyl)-3-methoxybenzoate and butyl chloroformate, methyl 4-[6-(butoxycarbonyl)amino-2,3,5-trimethylindol-1-ylmethyl]-3-methoxybenzoate (Example 39) was obtained in 99% yield as a white solid; partial NMR: 0.9 (t, 3H, CH2CH3), 1.3 (m,2H,CH2CH3), 1.5 (m,2H, CH2OCH2 0), 4.1 (t,2H,CH2O), 4.1 (t,2H,CH2O).

Sources & evidence

ORD record: ord-18d16db2602446aa85fbfd13c71764cd
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997844

Reaction notes

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