Sodium Hydroxide → HCID 86700405、化合物

HRID 879591ノート

反応式

HRID 879591 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][C:21]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([CH3:25])[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:34]([CH3:35])=[CH:33][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][C:21]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([CH3:25])[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86700404HCID 86700404、化合物

生成物 1

HCID 86700405HCID 86700405、化合物

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of (2S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-chlorophenyl)-2-methylmorpholino)-5-methylbenzo[d]thiazol-6-yl)acetate (63.7 mg, 0.101 mmol) in CH3OH/THF (1:1, 4 mL) was added NaOH (2N, 1 mL, 2 mmol), the resulting mixture was heated at 50° C. for 14 hr. The mixture was evaporated to a small volume, acidified to pH 3 and taken into partitioned between CH2Cl2 and brine. The organic layer was separated, dried (Na2SO4), filtered and evaporated to dryness. The residue was purified on CombiFlash (50% EtOAc/Hex) to give (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-chlorophenyl)-2-methylmorpholino)-5-methylbenzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C31H32Cl2N2O4S: 599.2, 601.2 (M+H+); found: 599.2, 601.2 (M+H+). 1H-NMR: 400 MHz, (CD3OD) δ: 7.62 (m, 1H), 7.44-7.53 (m, 5H), 7.32 (m, 3H), 5.13 (s, 1H), 4.31 (t, J=14.4 Hz, 1H), 3.81 (m, 1H), 3.62 (m, 1H), 3.44-3.53 (m, 3H), 2.50 (s, 3H), 1.46 (s, 3H), 0.95 (s, 9H).

後処理

  1. customThe mixture was evaporated to a small volume
  2. custominto partitioned between CH2Cl2 and brine
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified on CombiFlash (50% EtOAc/Hex)

出典と根拠

ORDレコード
ord-a451ca9b3ac14fea8b30754425a9a031
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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