Sodium cyanoborohydride → HCID 86727465、化合物

HRID 519093ノート

反応式

HRID 519093 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=O)[CH:9]1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:16]=[C:17]2[C:26](=[CH:27][CH:28]=1)[O:25][CH2:24][C:23]1[N:18]2[CH:19]([CH3:30])[C:20](=[O:29])[NH:21][N:22]=1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:14][C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][CH:28]=2)[O:25][CH2:24][C:23]2[N:18]3[CH:19]([CH3:30])[C:20](=[O:29])[NH:21][N:22]=2)[CH:9]1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 722080901-Azetidinecarboxylic acid, 2-methyl-3-oxo-, 1,1-dimethylethyl esterHCID 867272916-Amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

生成物 1

HCID 86727465HCID 86727465、化合物収率 18.5%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

To a mixture of 2-methyl-3-oxo-azetidine-1-carboxylic acid tert-butyl ester (crude, 1.17 mmol) in MeOH (5 mL) and AcOH (0.5 mL) was added 6-amino-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #2, Step E, 0.050 g, 0.215 mmol). The reaction mixture was stirred at ambient temperature for 0.5 h then NaBH3CN (0.068 g, 1.076 mmol) was added. The mixture was stirred at ambient temperature overnight then concentrated in vacuo. The residue was purified by preparative HPLC (Table 3, Method 24) to give 2-methyl-3-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-azetidine-1-carboxylic acid tert-butyl ester (0.016 g, 18%). LC/MS (Table 1, Method 5) Rt=1.087 min; MS m/z: 424 [M+23]+.

後処理

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (Table 3, Method 24)

出典と根拠

ORDレコード
ord-1caf26f4d96043e0a393d9e369bc6830
出典データセット
uspto-grants-2015_08
特許番号
US09115151B2

反応ノート

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