Methyl chloroformate → HCID 19003141, compound

HRID 2259294Notes

Reaction equation

Cl.[NH2:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=[O:5].Cl[C:27]([O:29][CH3:30])=[O:28]>>[CH3:30][O:29][C:27]([NH:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1)=[O:5])=[O:28]

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 19003122HCID 19003122, compound

Product 1

HCID 19003141HCID 19003141, compound

Procedure

Following the method of Example 18, 3,5-dimethylbenzyl 2-amino-3-(3-indolyl)propionate hydrochloride and methyl chloroformate gave the title compound after recrystallisation from ethyl acetate/petroleum ether, m.p. 128°-129° C. 1H NMR (360 MHz, CDCl3) δ8.04 (1H, s), 7.52 (1H, d, J=8.0 Hz), 7.32 (1H, d, J=8 Hz), 7.18 (1H, t, J=8 Hz), 7.09 (1H, t, J=8 Hz), 6.95 (1H, s), 6.83 (2H, s), 5.25 (1H, d, J=7.5 Hz), 5.00 (2H, dd, J=12 Hz), 4.73 (1H, m), 3.65 (3H, s), 3.29 (2H, d, J=5 Hz), 2.29 (6H, s).

Sources & evidence

ORD record: ord-df396b2e1d754587a840576fca7c492e
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472978

Reaction notes

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