Water → HCID 22287095, compound

HRID 901314Notes

Reaction equation

HRID 901314 reaction equation
C([O:5][C:6](=[O:52])[CH2:7][CH:8]1[CH2:13][CH:12]([CH2:14][CH2:15][N:16]2[CH:20](C(C)C)[CH:19](C(=O)NC3C=CC=CC=3)[CH:18](C3C=CC=CC=3)[CH:17]2C2C=CC(F)=CC=2)OB(C2C=CC=CC=2)O1)(C)(C)C.O.[O-2].[Ca+2]>C(#N)C>[N:16]1([CH2:15][CH2:14][CH2:12][CH2:13][CH2:8][CH2:7][C:6]([OH:52])=[O:5])[CH:20]=[CH:19][CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 6850728CalciumoxideHCID 58626912HCID 58626912, compound

Product 1

HCID 22287095HCID 22287095, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of (6-{2-[2-(4-Fluoro-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrolidin-1-yl]-ethyl}-2-phenyl-[1,3,2]dioxaborinan-4-yl)-acetic acid tert-butyl ester (100 g, 0.14 mol), water (3.0 L), acetonitrile (3.0 L) and calcium oxide (75 g, 1.35 mol) was stirred at 50-60° C. for 12 hours. After filtering the reaction mixture, the resulting clear filtrate was concentrated to about 3.0 L and washed with methyl tert-butyl ether (1.0 L). The aqueous layer was evaporated and the solid obtained was dissolved in acetonitrile (1.0 L). The solution was filtered and concentrated to yield [R-(R*R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, 1H-Pyrrole-1-heptanoic acid hemicalcium salt.

Workup

  1. filtrationAfter filtering the reaction mixture
  2. concentrationthe resulting clear filtrate was concentrated to about 3.0 L
  3. washwashed with methyl tert-butyl ether (1.0 L)
  4. customThe aqueous layer was evaporated
  5. customthe solid obtained
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-352c432f0480419ca923d2537211bf04
Source dataset
uspto-grants-2008_04
Patent number
US07361772B2

Reaction notes

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