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

HRID 1422623Notes

Reaction equation

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

Participants

Reactant 2

HCID 10928Ethyl 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 90313127{(S)-6-[(R)-4-(4-Ethoxycarbonyl-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 ethyl 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=1.02 min; Mass spectrum (ESI+): m/z=563 [M+H]+.

Sources & evidence

ORD record: ord-36bcc15d88524e17a5bf2604d0804e8b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927531B2

Reaction notes

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