Triethylamine → 3-t-Butoxycarbonylaminomethyl-2-thienylacetic acid

HRID 26996

反応式

HRID 26996 の反応式
[NH2:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C:9]([OH:11])=[O:10].C(N(CC)CC)C.[C:19]([O:23][C:24](N=[N+]=[N-])=[O:25])([CH3:22])([CH3:21])[CH3:20]>CC(C)=O>[C:19]([O:23][C:24]([NH:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C:9]([OH:11])=[O:10])=[O:25])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 159181433-Aminomethyl-2-thienylacetic acid

生成物 1

HCID 159181443-t-Butoxycarbonylaminomethyl-2-thienylacetic acid収率 92%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 3-aminomethyl-2-thienylacetic acid 8 (3.1 g, 18 m. moles) and triethylamine (8 g. 80 m moles) in 50% aqueous acetone (80 ml) was added dropwise t-butoxycarbonyl azide (5.7 g, 40 m moles) over a period of 20 mins. at 0° C. with vigorous stirring. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The concentrate was washed with ether (2×20 ml), adjusted to pH 2 with conc. HCl and extracted with ethyl acetate (2×50 ml). The ethyl acetate extracts were washed with saturated aqueous sodium chloride, dried over MgSO4, treated with charcoal and evaporated under reduced pressure. The residue was triturated with n-hexane and crystallized from n-hexane and benzene to give 4.5 g (92%) of colorless needles 9, melting at 62°-63° C.

後処理

  1. customat 0° C.
  2. concentrationconcentrated under reduced pressure
  3. washThe concentrate was washed with ether (2×20 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe ethyl acetate extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried over MgSO4
  7. additiontreated with charcoal
  8. customevaporated under reduced pressure
  9. customThe residue was triturated with n-hexane
  10. customcrystallized from n-hexane and benzene

出典と根拠

ORDレコード
ord-0ebb8843cadb45a19a8b61f469ed62b0
出典データセット
uspto-grants-1979_04
特許番号
US04151352

関連ノート

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