HCID 58818860, compound → HCID 58818861, compound

HRID 2375433Notes

Reaction equation

HRID 2375433 reaction equation
[CH3:1][O:2][C:3](=[O:23])/[C:4](/[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[CH:5]/[CH2:6][C:7]([CH3:11])([CH3:10])[CH:8]=[CH2:9]>CO>[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:5][CH2:6][C:7]([CH3:10])([CH3:11])[CH2:8][CH3:9]

Participants

3

Reactant 1

HCID 58818860HCID 58818860, compound

Product 1

HCID 58818861HCID 58818861, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

R,R-DIPAMP cyclooctadiene Rh(I) tetrfluoroborate (190 mg, 0.25 mmol, 0.04 eq) was added to a solution of (Z)-2-benzyloxycarbonylamino-5,5-dimethyl-hepta-2,6-dienoic acid methyl ester (2.00 g, 6.30 mmol, 1.00 eq) in dry methanol (20 mL) in a Paar hydrogenation flask. The reaction vessel was evacuated and flushed with a hydrogen atmosphere three times, then vigorously shaken under 50 psi of hydrogen overnight. The reaction mixture was concentrated in vacuo then filtered through a plug of silica gel using a gradient of ethyl acetate in hexanes as the eluant to provide (S)-2-benzyloxycarbonylamino-5,5-dimethyl-heptanoic acid methyl ester as a yellow oil (1.63 g, 81% yield); 1H NMR (CDCl3, 400 MHz) δ 0.74-0.90 (m, 9H), 1.10-1.30 (m, 4H), 1.58-1.70 (m, 1H), 1.75-1.90 (m, 1H), 3.75 (s, 3H), 4.30-4.40 (m, 1H), 5.14 (s, 2H), 5.24-5.33 (m, 1H), 7.30-7.37 (m, 5H); [α]20D=+15.57 c=2.00, CHCl3.

Workup

  1. customThe reaction vessel was evacuated
  2. customflushed with a hydrogen atmosphere three times
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. filtrationthen filtered through a plug of silica gel using a gradient of ethyl acetate in hexanes as the eluant

Sources & evidence

ORD record
ord-1fd1275c9e814bac9e07ee6d19884c0e
Source dataset
uspto-grants-2008_12
Patent number
US07465745B2

Reaction notes

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