tert-Butanol → t-Butyloxycarbonyl-4-{3-(2-benzyloxyphenyl)propyl]benzene-amine

HRID 2395039

反応式

HRID 2395039 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=C[C:21](C(O)=O)=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49][CH3:50])CC)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:21]([C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:23]=[CH:50][C:49]=1[NH2:46])=[O:34])([CH3:54])([CH3:53])[CH3:52]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

生成物 1

HCID 18973826t-Butyloxycarbonyl-4-{3-(2-benzyloxyphenyl)propyl]benzene-amine

実験手順

A mixture of 4-[3-(2-benzyloxyphenyl)propyl]benzene carboxylic acid (8.39 g), diphenylphosphoryl azide (5.74 ml) and triethylamine (7.1 ml) in t-butanol (80 ml) was heated under reflux in an argon atmosphere for 16 hours. The reaction mixture was evaporated to dryness and the residue partitoned between ethyl acetate and water. The ethyl acetate extract was washed once each with 2N HCl, water, saturated aqueous sodium bicarbonate solution and brine (20 ml each time) and dried (MgSO4). The solvent was evaporated and the residue subjected to flash chromatography eluted with a mixture of dichloromethane:hexane (1:1 v/v) to give N t-butyloxycarbonyl-4-{3-(2-benzyloxyphenyl)propyl]benzene-amine 7.69 g m.p. 86°-8° C. which was used directly in the next step.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux in an argon atmosphere for 16 hours
  3. customThe reaction mixture was evaporated to dryness
  4. extractionThe ethyl acetate extract
  5. washwas washed once each with 2N HCl, water, saturated aqueous sodium bicarbonate solution and brine (20 ml each time)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. washeluted with a mixture of dichloromethane:hexane (1:1 v/v)

出典と根拠

ORDレコード
ord-28b7cf6826bf4a3c962538dcb0786d6e
出典データセット
uspto-grants-1998_09
特許番号
US05811459

関連ノート

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