Sodium Hydroxide → 4-[9-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoic acid

HRID 1514281Notes

Reaction equation

HRID 1514281 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[O:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:27]4[O:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403438Ethyl 4-[9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate

Product 1

HCID 441290654-[9-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoic acidYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-[9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate (Preparation 68) (130 mg, 0.260 mmol) in ethanol was treated with sodium hydroxide (10.4 mg in 1 ml, 0.260 mmol). The reaction mixture was left standing at RT for 1 hour then evaporated. The resulting crude was partitioned between EtOAc/water, acidified with acetic acid, separated and the organivs dried over magnesium sulphate and evaporated. The title compound (61 mg) was obtained by trituration with ether as a white solid. δH (d6DMSO, 400 MHz): 1.36 (6H, d), 1.69 (2H, m), 2.23 (2H, t), 2.43 (2H, t), 3.05 (2H, m), 3.86 (2H, s), 4.07 (2H, m), 4.88 (1H, m), 7.20 (1H, t), 7.43-7.49 (2H, m), 7.78 (1H, dd), 8.09 (1H, dd), 8.17 (1H, d), 12.10 (1H, br. s); MS (ES−): C24H2635ClN3O5 requires 471; found 470 [M−H+].

Workup

  1. waitThe reaction mixture was left
  2. customthen evaporated
  3. customThe resulting crude was partitioned between EtOAc/water
  4. customseparated
  5. dry with materialthe organivs dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-75821d7e42814143a0c7d1d88054cc08
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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