Ammonium formate → tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate

HRID 1700978ノート

反応式

HRID 1700978 の反応式
[CH3:1][C:2]([CH3:45])([CH3:44])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:27]/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:32]([CH3:43])[CH:31]=1)[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5].C([O-])=O.[NH4+]>[Pd].CO>[CH3:44][C:2]([CH3:1])([CH3:45])[C@H:3]([NH:15][C:16]([C@H:18]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:32]([CH3:43])[CH:31]=1)[CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[O:17])[C:4]([NH:6][C@@H:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:8])=[O:5]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 59875764tert-butyl (3R,5E)-3-({[(1s)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hex-5-enoate

生成物 1

HCID 59875747tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate収率 90%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of tert-butyl (3R,5E)-3-({[(1s)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hex-5-enoate (615 mg, 1.00 mmol), ammonium formate (310 mg, 4.9 mmol) and 10% palladium on charcoal (65 mg) in methanol (8 mL) was stirred at 20° C. for 16 h. The mixture was filtered through Arbocel filter aid and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated under reduced pressure to give tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate (550 mg, 90%), as a foam, which was taken onto the next step without purification.

後処理

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3f97881226954414852f52ac7ae18cd0
出典データセット
uspto-grants-2002_02
特許番号
US06350907B1

反応ノート

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