Methanol → HCID 57871405, compound

HRID 550225Notes

Reaction equation

HRID 550225 reaction equation
[Li+].[OH-].O.C[O:5][C:6](=[O:43])[CH2:7][NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]([CH2:41][CH3:42])([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH2:38][CH3:39])[CH:32]([OH:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:40])[CH:25]=3)[CH2:22][CH3:23])[CH:17]=2)[CH:12]=1)=[O:10].CO>C1COCC1>[CH2:22]([C:21]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:43])=[O:5])=[O:10])[CH:20]=[CH:19]2)([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH2:38][CH3:39])[CH:32]([OH:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[C:26]([CH3:40])[CH:25]=1)[CH2:41][CH3:42])[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 57871407HCID 57871407, compound

Product 1

HCID 57871405HCID 57871405, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2.5 M LiOH/H2O (0.82 ml, 2.04 mmol) to diastereomeric isomer pair 1 of 2-[6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-naphthalene-2-carbonylamino]acetic acid methyl ester (373 mg, 0.681 mmol) in THF (3 ml), and MeOH (1.5 ml). Stir the reaction for 14 h; then partition the reaction mixture between Et2O and 1N HCl. Dry the organic layer with MgSO4, concentrate and triturate the residue with CH2Cl2/MeOH/hexanes to give the title compound as a white solid (310 mg, 85%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.2 Hz, 6H), 0.93 (t, J=8.0 Hz, 3H), 0.93 (s, 9H), 1.68 (m, 1H), 1.81 (m, 1H), 2.11 (s, 3H), 2.15 (q, 4H), 3.28 (s, 1H), 4.27 (dd, J=5.2, 3.6 Hz, 1H), 4.35 (d, J=4.8 Hz, 2H), 6.63 (d, J=8.0 Hz, 1H), 6.83 (t, J=4.8 Hz, 1H), 6.89 (s, 1H), 6.93 (dd, J=6.4, 2.2 Hz, 1H), 7.18 (dd, J=7.2, 1.6 Hz, 1H), 7.74 (d, J=8.8 Hz, 1H), 7.88 (m, 3H), 8.27 (s, 1H). High Res. ES-MS: 556.3046; calc. for C33H43NO5+Na: 556.3040.

Workup

  1. customthe reaction for 14 h
  2. customthen partition the reaction mixture between Et2O and 1N HCl
  3. dry with materialDry the organic layer with MgSO4
  4. concentrationconcentrate
  5. customtriturate the residue with CH2Cl2/MeOH/hexanes

Sources & evidence

ORD record
ord-3841651dee4b4e2c8be071ad1e9fdce6
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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