Hydrochloric Acid → 3-Acetoxy-5-biphenyl-4-yl-pentanoic acid tert-butyl ester

HRID 1297256Notes

Reaction equation

HRID 1297256 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13](=[O:31])[CH2:14][CH:15]([OH:30])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:8]([O:12][C:13](=[O:31])[CH2:14][CH:15]([O:30][C:1](=[O:3])[CH3:2])[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:22][CH:23]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 116240165-Biphenyl-4-yl-3-hydroxy-pentanoic acid tert-butyl ester2×

Product 1

HCID 586751293-Acetoxy-5-biphenyl-4-yl-pentanoic acid tert-butyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Acetic anhydride (40 μL, 0.42 mmol) was added to a stirred solution of 5-biphenyl-4-yl-3-hydroxy-pentanoic acid tert-butyl ester (Intermediate 3, 54 mg, 0.17 mmol), 4-dimethylaminopyridine (5.0 mg, 41 μmol) and pyridine (54 μL, 0.66 mol) in dichloromethane (1 mL) at room temperature under nitrogen. Stirring was continued for 12 hours at room temperature before the addition of 2 M hydrochloric acid (5 mL) and dichloromethane (5 mL). The phases were separated and aqueous phase extracted with dichloromethane (3×5 mL). The organic phases were combined, washed with brine (5 mL) and dried (MgSO4). The solvent was removed by evaporation under reduced pressure to give the title compound (45 mg, 74%) as a colourless gum. LC/MS: 3.91 min; z/e 386, calcd (M+NH4) 386. 1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.52 (2 H), 7.42 (2 H), 7.33 (1 H), 7.25 (2 H), 5.29 (1 H), 2.70 (2 H), 2.53 (2 H), 2.05 (3 H), 1.97 (2H), 1.42 (9 H).

Workup

  1. customThe phases were separated
  2. extractionaqueous phase extracted with dichloromethane (3×5 mL)
  3. washwashed with brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-62d54a42bcec4fe7a53ed57b89d42e65
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

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