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 55729

Reaktionsgleichung

Reaktionsgleichung von HRID 55729
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product of Example 68D (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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5b7e921903e24c19a60a61f2c599d61d
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05625072

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