3-Methoxycyclobutane-1-carboxylic acid → HCID 53244542, compound

HRID 587379Notes

Reaction equation

HRID 587379 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[CH3:25][O:26][CH:27]1[CH2:30][CH:29]([C:31](O)=[O:32])[CH2:28]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:31]([CH:29]3[CH2:30][CH:27]([O:26][CH3:25])[CH2:28]3)=[O:32])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 229347623-Methoxycyclobutane-1-carboxylic acidHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 53244542HCID 53244542, compound

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(4-chloro-phenyl)-1-(3-methoxy-cyclobutanecarbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 3-methoxycyclobutanecarboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a light brown oil. MS m/e: 461.2 [M+H]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-5b58714a2c1d4c61a31ff5667eb59cda
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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