Lithium Hydroxide → HCID 57988338, compound

HRID 1666537Notes

Reaction equation

HRID 1666537 reaction equation
[C:1]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([S:34]([CH2:37][CH2:38][CH3:39])(=[O:36])=[O:35])[CH2:11][N:10]([C:12](=[O:29])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C@H:9]([C:30]([O:32]C)=[O:31])[CH2:8]2)=[CH:3][CH:2]=1.[OH-].[Li+]>C1COCC1.CO.O>[C:1]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([S:34]([CH2:37][CH2:38][CH3:39])(=[O:36])=[O:35])[CH2:11][N:10]([C:12](=[O:29])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C@H:9]([C:30]([OH:32])=[O:31])[CH2:8]2)=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57988330HCID 57988330, compound

Product 1

HCID 57988338HCID 57988338, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(propylsulfonyl)pyrrolidine-2-carboxylate (1.52 g, 2.372 mmol) in THF (20.00 mL) and MeOH (20 mL) was added pre-made solution of lithium hydroxide (0.199 g, 4.74 mmol) in water (20.00 mL). The formed cloudy solution was stirred at rt for 3 h. Removed the volatiles in vacuo. The residue was acidified with 1M HCl to pH 3, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated in vacuo to afford the desired product (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(propylsulfonyl)pyrrolidine-2-carboxylic acid (1.45 g, 2.198 mmol, 93% yield) as a white foam. 1H NMR (400 MHz, MeOD) δ ppm 0.97 (t, J=7.53 Hz, 3 H) 1.36-1.55 (m, 12 H) 1.55-1.82 (m, 4 H) 2.10 (q, J=6.61 Hz, 2 H) 2.81 (dd, J=8.66, 6.65 Hz, 2 H) 2.91 (dd, J=12.92, 10.42 Hz, 1 H) 3.28 (d, J=7.28 Hz, 1 H) 4.20 (dd, J=9.91, 7.40 Hz, 1 H) 4.37 (d, J=11.04 Hz, 1 H) 4.52 (t, J=6.90 Hz, 1 H) 4.95 (dd, J=10.16, 1.13 Hz, 2 H) 4.98-5.07 (m, 1 H) 5.13 (d, J=11.04 Hz, 1 H) 5.77-5.94 (m, 1 H) 7.33-7.42 (m, 1 H) 7.48 (t, J=7.53 Hz, 2 H) 7.65 (d, J=7.53 Hz, 2 H) 7.72-7.78 (m, 2 H) 7.93 (d, J=8.28 Hz, 2 H). LC-MS (retention time: 1.99 min, method A), MS m/z 627 (M+H).

Workup

  1. customRemoved the volatiles in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-42f0d2b254504db2808f191f5e5787bb
Source dataset
uspto-grants-2011_10
Patent number
US08044023B2

Reaction notes

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