1-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid → HCID 58303017, compound

HRID 587381Notes

Reaction equation

HRID 587381 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.[C:25]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH:34]([C:37](O)=[O:38])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([N:32]1[CH2:36][CH2:35][CH:34]([C:37]([N:14]2[CH2:13][C@@H:12]([N:10]([C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:24])[CH3:11])[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15]2)=[O:38])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 67233751[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 58303017HCID 58303017, compound

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound 3-{(3R,4S)-3-(4-chloro-phenyl)-4-[(4-fluoro-phenoxycarbonyl)-methyl-amino]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl 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 rac-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a light yellow oil. MS m/e: 546.2 [M]+.

Workup

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

Sources & evidence

ORD record
ord-d84b6ec508f04affa93f8b36eca09d8f
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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