Diisopropylethylamine → (S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216903노트

반응식

HRID 216903 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([I:30])=[CH:26][CH:25]=1)[C:20]([NH2:22])=[O:21].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH2:22][C:20](=[O:21])[C@@H:19]([NH:18][C:15]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:17])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([I:30])=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 447705(S)-2-Amino-3-(4-iodophenyl)propanamideHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate수율 118.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxylic acid (0.801 g), (S)-2-amino-3-(4-iodophenyl)propanamide (Example 1, step (ii), 0.947 g) and N-ethyl-N-isopropylpropan-2-amine (1.422 mL) were dissolved in DMF (10 mL) and to the solution was added TBTU (1.573 g). The reaction mixture was stirred, at room temperature, for 2 days. The reaction mixture was evaporated to dryness dissolved in dichloromethane (20 mL) and evaporated onto silica. The silica was put on the top of a silica column and eluted with 20% ethyl acetate in isohexane then 50% ethyl acetate in isohexane then 100% ethyl acetate followed by 10% then 20% methanol in ethyl acetate to afford the sub-titled compound (2.00 g).

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in dichloromethane (20 mL)
  3. customevaporated onto silica
  4. washeluted with 20% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-2a58ec582cf8408c99d8e821d2fca994
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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