Tetrahydrofuran → HCID 101747281, compound

HRID 2258299Notes

Reaction equation

HRID 2258299 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)[CH:14]([CH3:16])[CH3:15])[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].[O:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH2:38]([O:34][CH2:12][C@@H:13]([CH2:17][CH:10]([OH:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12][C@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)[CH:14]([CH3:16])[CH3:15])[CH:14]([CH3:16])[CH3:15])[C:37]1[CH:3]=[CH:1][CH:2]=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 11590225tert-Butyl [(2S,4S)-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methyl-1-oxohexan-2-yl]carbamate

Product 1

HCID 101747281HCID 101747281, compound

Conditions

Temperature
55 °C

Procedure

The reaction mixture is stirred for a further 20 minutes at 55° C. and then cooled to 5° C. A solution of 2(S)-(tert-butoxycarbonyl)amino-4(S)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-5-methyl-hexanal (190 g) in tetrahydrofuran (700 ml) is then added dropwise. The reaction mixture is stirred for a further 3 hours at room temperature, then at 5° C. saturated ammonium chloride solution is added and the mixture is extracted with diethyl ether. The organic phases are concentrated and purified by FC (4 kg of silica gel, ethyl acetate/hexane 1:3). The title compound is obtained in the form of a colourless oil (139 g): Rf (ethyl acetate/hexane 1:2)=0.26; HPLC Rt =22.7 and 22.8 min ((4:6)-diastereoisomeric mixture).

Workup

  1. temperaturecooled to 5° C
  2. stirringThe reaction mixture is stirred for a further 3 hours at room temperature
  3. extractionthe mixture is extracted with diethyl ether
  4. concentrationThe organic phases are concentrated
  5. custompurified by FC (4 kg of silica gel, ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-bfb90797dc9b4900b4c445295340c58f
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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