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Sodium Hydroxide → 4-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 1643572
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HRID 1643572 반응식
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([N:27]3[CH2:30][CH2:29][CH2:28]3)=[O:26])=[CH:21][CH:20]=2)[C:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=2[CH:8]=1)=[O:6]>CO>[N:27]1([C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][C:16]3[C:10]4[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=4[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:17]=3)=[CH:24][CH:23]=2)=[O:26])[CH2:30][CH2:29][CH2:28]1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 595602514-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

생성물 1

HCID 595598464-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid수율 77.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

Aqueous NaOH (3 N, 2.1 mL, 6.3 mmol) was added to a solution of 4-[4-(azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (35b) (802 mg, 2.10 mmol) in 10 mL CH3OH. The mixture was heated to 60° C. for 3 hr, concentrated, diluted with H2O (60 mL) and acidified with 1N aqueous HCl to Ph ˜1. The aqueous phase was extracted with CH2Cl2 (60 mL), dried with MgSO4 and concentrated to give a white solid (598 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.99 (s, 1 H) 7.67 (d, J=7.33 Hz, 2 H) 7.02-7.10 (m, 3 H) 6.99 (s, 1 H) 4.32 (s, 2 H) 4.03 (s, 2 H) 2.89 (s, 2 H) 2.21-2.30 (m, 2 H) 1.42 (s, 6 H); LCMS for C21H21NO5 m/z 468.00 (M+H)+.

후처리

  1. concentrationconcentrated
  2. additiondiluted with H2O (60 mL)
  3. extractionThe aqueous phase was extracted with CH2Cl2 (60 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-de868da45c67484db8e7af61c7be43aa
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119624B2

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