Hydrochloric Acid → Prosta-​5,​13-​dien-​1-​oic acid, 15-​hydroxy-​11,​16,​16-​trimethyl-​9-​oxo-​, (5Z,​11α,​13E,​15R)​-

HRID 637774Notes

Reaction equation

HRID 637774 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:25]C(=O)C)[C:18]([CH3:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([CH3:29])[CH2:12][C:11]1=[O:30].[OH-].[Na+].Cl>CO>[OH:25][C@@H:17]([C:18]([CH3:23])([CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])/[CH:16]=[CH:15]/[C@@H:14]1[C@@H:10]([CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])[C:11](=[O:30])[CH2:12][C@H:13]1[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70392134HCID 70392134, compound

Product 1

HCID 6917757Prosta-​5,​13-​dien-​1-​oic acid, 15-​hydroxy-​11,​16,​16-​trimethyl-​9-​oxo-​, (5Z,​11α,​13E,​15R)​-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of optically active (5Z,11alpha,13E,15R)-15-acetyloxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid methyl ester (3.2 g) in methanol (32 mL) was treated with 4N NaOH (6.4 mL) and stirred under argon for 20 hours. The solution was acidified with 2N HCl and the product recovered by ethyl acetate extraction. There was thus obtained 3.0 g (~100%) of crude optically active (5Z,11alpha,13E,15R)-15-hydroxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid as a yellow oil.

Workup

  1. customthe product recovered by ethyl acetate extraction

Sources & evidence

ORD record
ord-a0c38c7cd57d40efa72e9a44f783d8e5
Source dataset
uspto-grants-1985_12
Patent number
US04558140

Reaction notes

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