Lithium hydroxide, monohydrate → 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 1957584Notes

Reaction equation

HRID 1957584 reaction equation
O[Li].O.C[O:5][C:6](=[O:45])[C@@H:7]([NH:35][S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:38])=[O:37])[CH2:8][NH:9][C:10]([C:12]1[O:16][N:15]=[C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:13]=1)=[O:11].OS([O-])(=O)=O.[Na+]>C1COCC1>[C:28]([N:25]1[CH2:26][CH2:27][CH:22]([CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:14]2[CH:13]=[C:12]([C:10]([NH:9][CH2:8][C@H:7]([NH:35][S:36]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)(=[O:38])=[O:37])[C:6]([OH:45])=[O:5])=[O:11])[O:16][N:15]=2)[CH2:23][CH2:24]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516919Sodium BisulfateHCID 867529453-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester

Product 1

HCID 867529463-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanineYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (35 mg, 0.87 mmol, 4-6 (176 mg, 0.29 mmol), and 20% aq. THF (10 mL) was stirred at ambient temperature for 1 h. The reaction mixture was acidified with 1M NaHSO4 and extracted with EtOAc (3×). The combined extracts were dried (MgSO4) and concentrated to give 4-7 (171 mg) as a foam. Rf 0.73 (silica, 9:0.5:0.5 CH2Cl2 /CH3OH/AcOH). ##STR49## 3-[4-(Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-β-alanine (4-8)

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-697bf43747c144eb8a3877f3458d4f34
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

Loading…