Acetyl chloride → HCID 53244606, compound

HRID 587409Notes

Reaction equation

HRID 587409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:39])[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:24]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][N:33]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[C:40](Cl)(=[O:42])[CH3:41]>>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:16]2[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:39])[CH3:11])[CH2:13][N:14]([C:24]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][C:35]([O:38][C:40](=[O:42])[CH3:41])=[CH:34][N:33]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:15]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 53244607HCID 53244607, compound

Product 1

HCID 53244606HCID 53244606, compound

Procedure

A mixture of [(3S,4R)-4-(4-Chloro-phenyl)-1-(5′-hydroxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (example 320, crude) was treated with acetyl chloride and the mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions the title compound as light yellow solid. MS m/e: 595.4 [M+H]+.

Workup

  1. customthe mixture was purified by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions the title compound as light yellow solid

Sources & evidence

ORD record
ord-185e68857b72401397c0d6635060218a
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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