Methanol → HCID 69906473, compound

HRID 1107177Notes

Reaction equation

HRID 1107177 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][C@@H:10]([C@H:18]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]([O:13]C(C)(C)C)=[O:12].CO>C(Cl)Cl>[OH:8][CH2:9][CH:10]([CH:18]([S:29]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)(=[O:30])=[O:31])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 54413126HCID 54413126, compound

Product 1

HCID 69906473HCID 69906473, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (5 mL) is added to a solution of (±)-t-butyl (2R*,3R*)-2-hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoate (3.1 g, 6.7 mmol) in CH2Cl2 (20 mL). The reaction is monitored by TLC analysis (5% MeOH in CH2Cl2) and before all of the ester is consumed the reaction is concentrated and azeotroped with CHCl3 (3×15 mL). The crude product is purified by column chromatography (silica, 5% MeOH in CH2Cl2) to yield pure (±)-(2R*, 3R*)-2-Hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoic acid (1.4 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=7.0 Hz, 2H), 7.25-7.11 (m, 3H), 7.07-6.93 (m, 4H), 6.5-5.7 (bs, 1H), 4.34-4.26 (bm, 1H), 3.95-3.89 (bm, 1H), 3.82 (s, 3H), 3.81-3.69 (bm, 1H), 3.13-3.06 (bm, 1H), 2.46-2.37 (bm, 2H), 1.75-1.67 (bm, 2H), 1.48-1.30 (bm, 3H), 1.22-1.09 (bm, 1H); MS (FAB) m/e 406 (M+H)+.

Workup

  1. custombefore all of the ester is consumed the reaction
  2. concentrationis concentrated
  3. customazeotroped with CHCl3 (3×15 mL)
  4. customThe crude product is purified by column chromatography (silica, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6695ce4becf147d3835b5bad63952585
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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