Sodium triacetoxyborohydride → (2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

HRID 490255ノート

反応式

HRID 490255 の反応式
[NH2:1][CH:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].[C:25]([O:29][C:30](=[O:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH:33]=O)([CH3:28])([CH3:27])[CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:25]([O:29][C:30](=[O:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][NH:1][CH:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4])([CH3:28])([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 222387982-(1-amino-2-methylpropyl)-3-benzyl-7-chloroquinazolin-4(3H)-one

生成物 1

HCID 69074256(2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (WO 0130768) (1.09 g, 3.19 mmol) and (1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (Seki et. al. Chem. Pharm. Bull. 1996, 44, 2061) (0.59 g, 3.19 mmol) in dichloromethane (80 mL) was added sodium triacetoxyborohydride (1.01 g, 4.79 mmol). The resultant cloudy mixture was maintained at ambient temperature for 4 hours, at which time it was quenched with brine (75 mL) and stirred vigorously for 10 minutes. The aqueous layer was extracted with dichloromethane (50 mL) and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give (±)-{2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (1.62 g, 99%) as a yellow solid which was used in the subsequent step without purification.

後処理

  1. customwas quenched with brine (75 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f32aac740bec4cf993ac9787ee9c6101
出典データセット
uspto-grants-2009_05
特許番号
US07528137B2

反応ノート

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