Ethanol → HCID 86753204, compound

HRID 399342Notes

Reaction equation

HRID 399342 reaction equation
C([O:5][NH:6][C:7](=[O:49])[C@H:8]([N:30]([S:38]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)(=[O:40])=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1)[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:16])[CH2:11][CH2:10]1)(C)(C)C.C(O)C.C(Cl)[Cl:54]>>[ClH:54].[OH:5][NH:6][C:7](=[O:49])[C@H:8]([N:30]([S:38]([C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)(=[O:40])=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1)[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6344DichloromethaneHCID 18665834HCID 18665834, compound

Product 1

HCID 86753204HCID 86753204, compound

Conditions

Temperature
-10 °C

Procedure

N-(t-Butyloxy)-2-(R)-[(4-methoxybenzenesulfonyl)(4-picolyl)amino]-2-[(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl]acetamide (3 g, 4.65 mmol) is dissolved in methylene chloride (100 ml) containing ethanol (0.27 ml, 4.6 mmol) and the reaction mixture is cooled to -10° C. Hydrochloric acid gas (from a lecture bottle) is bubbled trough the solution for 15 minutes. The flask is sealed, the reaction mixture is allowed to slowly warm to room temperature and stirred at room temperature for 6 days. The reaction mixture is concentrated in vacuo to provide N-hydroxy-2-(R)-[(4-methoxy-benzenesulfonyl) (4-picolyl)amino]-2- [(N-(2-(1-naphthyl)-ethoxycarbonyl))-4-piperidinyl]acetamide hydrochloride as a white solid, m.p. >137° C. (dec).

Workup

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled trough the solution for 15 minutes
  2. customThe flask is sealed
  3. temperatureto slowly warm to room temperature
  4. concentrationThe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-df609be62c83498783f0feb6d6dddfba
Source dataset
uspto-grants-1998_10
Patent number
US05817822

Reaction notes

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