Sodium borohydride → 5-(benzyloxy)-8-({benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 749236ノート

反応式

HRID 749236 の反応式
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:24])[CH:21](O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+]>C(Cl)Cl.CO.C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:24])[CH2:21][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([C:20](=[O:24])[CH2:21][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 10914757N-benzyl-6-(4-phenylbutoxy)hexan-1-amineHCID 231061485-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one

生成物 2

HCID 693159345-(Benzyloxy)-8-(2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-oneHCID 693175385-(benzyloxy)-8-({benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-2H-1,4-benzoxazin-3(4H)-one収率 56.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-(benzyloxy)-8-(dihydroxyacetyl)-2H-1,4-benzoxazin-3(4H)-one (DE 3134590 A1) (150 mg) in dry DCM (2 ml) was treated with acetic acid and N-benzyl-6-(4-phenylbutoxy)hexan-1-amine (320 mg) (Tetrahedron Letters. 1994, 35, 9375) and stirred for 4 hr. Sodium triacetoxyborohydride (216 mg) was added and the reaction mixture stirred at room temperature for 3 days. Sodium borohydride (35 mg) in methanol (2 ml) was added and stirring continued for a further 2 h. The reaction mixture was quenched with water and partitioned between water and DCM. The organic phase was dried and concentrated in vacuo. The residue was purified by chromatography (Hexane-EtOAc, SPE) to give the title compound as a mixture with 5-(benzyloxy)-8-({benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-2H-1,4-benzoxazin-3(4H)-one (81.6 mg).

後処理

  1. stirringthe reaction mixture stirred at room temperature for 3 days
  2. stirringstirring
  3. waitcontinued for a further 2 h
  4. customThe reaction mixture was quenched with water
  5. custompartitioned between water and DCM
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (Hexane-EtOAc, SPE)

出典と根拠

ORDレコード
ord-51a85d211ac34e3da3865362d14542e6
出典データセット
uspto-grants-2008_07
特許番号
US07402598B2

反応ノート

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