Dichloromethane → (S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester

HRID 391858ノート

反応式

HRID 391858 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH:14]=O)=[CH:9][CH:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:35][O:36][C:37]([C@@H:39]1[CH2:48][C:47]2[C:42](=[CH:43][C:44](O)=[C:45]([NH2:49])[CH:46]=2)[CH2:41][N:40]1[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:38].C(Cl)Cl>ClCCCl.O>[CH3:35][O:36][C:37]([CH:39]1[CH2:48][C:47]2[CH:46]=[C:45]3[C:44]([O:16][C@@H:13]([C:10]4[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]5[CH:17]=[CH:18][C:19]([Cl:20])=[C:2]([Cl:1])[CH:3]=5)=[CH:12][CH:11]=4)[CH2:14][NH:49]3)=[CH:43][C:42]=2[CH2:41][N:40]1[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:38]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59337426(S)-6-amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl esterHCID 86654900[4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde

生成物 1

HCID 66719396(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester収率 71.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

実験手順

[4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde (616 mg) was dissolved in DCE (25 mL) and sodium triacetoxyborohydride (520 mg) and (S)-6-amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester (644 mg). The mixture was stirred overnight at room temperature. DCM (50 mL) was added to the reaction mixture and poured into water (25 mL). The organic layer was washed with 10% Na2CO3 solution and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (hexanes/ethyl acetate from 90:10 to 70:30) to afford (S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester (855 mg).

後処理

  1. washThe organic layer was washed with 10% Na2CO3 solution and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography (hexanes/ethyl acetate from 90:10 to 70:30)

出典と根拠

ORDレコード
ord-50dcbcf0437b4c8e98184544c04dd442
出典データセット
uspto-grants-2013_02
特許番号
US08383644B2

反応ノート

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