Isopropyl chloroformate → {(S)-6-[(R)-4-(4-Isopropoxycarbonyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422625Notes

Reaction equation

Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH3:8][O:9][C:10](=[O:42])[CH2:11][C@H:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][C@H:22]3[C:30]4[C:25](=[C:26]([CH2:35][N:36]5[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]5)[C:27]([C:31]([F:34])([F:33])[F:32])=[CH:28][CH:29]=4)[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1>>[CH3:8][O:9][C:10](=[O:42])[CH2:11][C@H:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][C@H:22]3[C:30]4[C:25](=[C:26]([CH2:35][N:36]5[CH2:37][CH2:38][N:39]([C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])[CH2:40][CH2:41]5)[C:27]([C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=4)[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

Reactant 2

HCID 7917Isopropyl chloroformate

HCID 90313619{(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Product 1

HCID 90313678{(S)-6-[(R)-4-(4-Isopropoxycarbonyl-piperazin-1-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Procedure

The title compound is prepared from isopropyl chloroformate and {(S)-6-[(R)-4-piperazin-1-ylmethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester following a procedure analogous to that described for Intermediate 27. LC (method 4): tR=1.05 min; Mass spectrum (ESI+): m/z=577 [M+H]+.

Sources & evidence

ORD record: ord-74bfe72f983b4a08ae8053aed9974730
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927531B2

Reaction notes

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