4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate → Thiazol-5-ylmethyl ((1S,2S,4S)-1-benzyl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-hydroxy-5-phenylpentyl)carbamate

HRID 375232

반응식

HRID 375232 반응식
[NH2:1][C@H:2]([C@@H:10]([OH:28])[CH2:11][C@@H:12]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+](C1C=CC([O:38][C:39]([O:41][CH2:42][C:43]2[S:47][CH:46]=[N:45][CH:44]=2)=O)=CC=1)([O-])=O>CN(C=O)C>[C:24]([O:23][C:21]([NH:20][C@@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:11][C@H:10]([OH:28])[C@@H:2]([NH:1][C:39]([O:41][CH2:42][C:43]1[S:47][CH:46]=[N:45][CH:44]=1)=[O:38])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:22])([CH3:25])([CH3:27])[CH3:26]

참가 물질

4

반응물 2

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 119979265-tert-Butyloxycarbonylamino-2-amino-3-hydroxy-1,6-diphenylhexane, (2S,3S,5S)-

생성물 1

HCID 22858342Thiazol-5-ylmethyl ((1S,2S,4S)-1-benzyl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-hydroxy-5-phenylpentyl)carbamate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The product of Example 22D (6.0 g , 15.6 mmoles) was dissolved in 60 mL of DMF under nitrogen atmosphere. To this stirred solution at room temperature was added 5-(p-nitrophenyloxycarbonyloxymethyl)thiazole (4.67 g, 15.6 mmole) and the resulting solution was stirred for 4 h. The solvent was removed under reduced pressure by rotary evaporation and the residue dissolved in 150 mL EtOAc. This solution was washed with 5×75 mL 1N NaOH solution, 100 mL brine, dried over Na2SO4. The solvent was removed to afford 8.02 g of a slightly yellowish oil. This material was crystallized from 30 mL EtOAc and 40 mL hexane to afford 6.53 g (80%) of the desired product as a white solid. mp 118°-120° C. H 1NMR (CDCl3) δ8.79 (s, 1H), 7.83 (s, 1H), 7.30-7.15 (m, 8H), 7.08 (m, 2H), 5.23 (s, 2H), 5.14 (d, 1H, J=9 Hz), 4.52 (m, 1H), 3.92-3.72 (m, 3H), 3.65 (m, 1H), 2.85 (d-apparent, 2H, J=7.5 Hz), 2.72 (d-apparent, 2H, J=7 Hz), 1.61 (m, 2H), 1.38 (s, 9H). CIMS m/z (526) (M+H)+, 543 (M+18)+.

후처리

  1. customThe solvent was removed under reduced pressure by rotary evaporation
  2. dissolutionthe residue dissolved in 150 mL EtOAc
  3. washThis solution was washed with 5×75 mL 1N NaOH solution, 100 mL brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customto afford 8.02 g of a slightly yellowish oil
  7. customThis material was crystallized from 30 mL EtOAc and 40 mL hexane

출처 및 근거

ORD 기록
ord-1700a49b22434124a49758bcbe09cdbf
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484801

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