Water → ((6S,8S)-6-(Anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetic acid

HRID 481256Notes

Reaction equation

HRID 481256 reaction equation
[CH2:1]([C@@:4]1([CH3:45])[C:8]2=[N:9][CH:10]=[C:11]([N:14]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:13])[N:7]2[C@H:6]([C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:37])[CH2:5]1)[CH:2]=C.[OH2:46].CC#N.C(Cl)(Cl)(Cl)Cl.[OH2:55]>>[NH:38]([C:36]([C@H:6]1[N:7]2[C:12](=[O:13])[C:11]([N:14]([C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:24])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=3)=[CH:10][N:9]=[C:8]2[C@@:4]([CH2:1][C:2]([OH:55])=[O:46])([CH3:45])[CH2:5]1)=[O:37])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 962WaterHCID 22592919water acetonitrile CCl42×HCID 86587576(6S)-N-Phenyl-3-[3-(trifluoromethyl)benzyl(benzyloxycarbonyl)amino]-4-oxo-8beta-allyl-8-methyl-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6alpha-carboxamide

Product 1

HCID 69972821((6S,8S)-6-(Anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetic acid

Procedure

To a solution of 117a (1.073 g, 1.740 mmol) in 15.4 mL CH3CN/CCl4/H2O (2:2:3), were added NaIO4 (1.56 g, 7.31 mmol) and a solution of RuCl3.H2O (18 mg, 0.087 mmol) in 2.25 mL of CH3CN/CCl4/H2O (2:2:3). The mixture was stirred vigorously for 16 h, then was poured into H2O and extracted with CH2Cl2 (2×). The combined organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to afford 1.17 g of 117b as a brown foam, which was used in the following step without further purification. MS (ESI) 657.3 (M+Na+); 633.4 (M−H+).

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de297439c1de407cbcc1407eb6661969
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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