Triethylamine → (R)-2-[(4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester

HRID 908719ノート

反応式

HRID 908719 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:17]=2)[C:12]([CH2:26][O:27][CH3:28])=[N:11][C:10]=1[C:29](O)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.ClC(OCC(C)C)=O.Cl.[C:48]([O:52][C:53](=[O:57])[C@@H:54]([CH3:56])[NH2:55])([CH3:51])([CH3:50])[CH3:49]>C(Cl)Cl>[C:48]([O:52][C:53](=[O:57])[C@H:54]([NH:55][C:29]([C:10]1[N:11]=[C:12]([CH2:26][O:27][CH3:28])[C:13]2[C:18]([C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:17][CH:16]=[C:15]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:14]=2)=[O:30])[CH3:56])([CH3:51])([CH3:50])[CH3:49]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 16211919D-Alanine tert-butyl ester hydrochlorideHCID 667128304-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid

生成物 1

HCID 66712878(R)-2-[(4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid tert-butyl ester収率 85.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid (79 mg, 0.19 mmol), NEt3 (56 μl, 0.4 mmol), and CH2Cl2 (5 ml) cooled with an ice bath was added ClCO2iBu (26.5 μl, 0.2 mmol) with stirring. After stirring for 15 min (R)-alanine tert-butyl ester hydrochloride (36 mg, 0.2 mmol) was added and the mixture was allowed to warm up to ambient temperature overnight with stirring. Subsequently; the mixture was concentrated in vacuo. To the residue was added water (10 ml) and a few drops of aqueous 6N HCl. The mixture was extracted with EtOAc (2×15 ml). The organic phase was dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography on silica gel using EtOAc as the eluent gave the title compound as a tan oil (88 mg); MS-(+)-ion: M+23=565.2.

後処理

  1. temperaturecooled with an ice bath
  2. additionwas added
  3. stirringwith stirring
  4. concentrationthe mixture was concentrated in vacuo
  5. additionTo the residue was added water (10 ml) and a few drops of aqueous 6N HCl
  6. extractionThe mixture was extracted with EtOAc (2×15 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-35771727bdaf40bb80da5b4470f9353e
出典データセット
uspto-grants-2011_09
特許番号
US08017625B2

反応ノート

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