Water → 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetic acid

HRID 1776551ノート

反応式

HRID 1776551 の反応式
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH2:24][C:25]([O:27]C)=[O:26])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH2:24][C:25]([OH:27])=[O:26])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH:21]1[CH2:22][CH2:23]1)[S:9]([CH3:12])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 89455750methyl 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetate

生成物 1

HCID 894599492-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetic acid収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetate (1.2 g, 2.90 mmol) in THF:water=1:1 (35 ml), LiOH (0.695 g, 29.0 mmol) was added, and the mixture was reacted for 30 minutes at RT. THF was evaporated, and the aqueous residue was acidified with HCl 6N (pH=7). The mixture was extracted with EtOAc (3×), and the combined organic layers were dried over Na2SO4. The solvent was removed under vacuum affording 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetic acid (1.1 g, 2.75 mmol, 95% yield, MS/ESI+ 400.0 [MH]+). This intermediate was used without any additional purification.

後処理

  1. customthe mixture was reacted for 30 minutes at RT
  2. customTHF was evaporated
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-73aef233ab1440ffb53c1b260de60261
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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