Hexane → N''-[N-METHOXYCARBONYL-L-VALYL]-N-[(S)-3,3,3-TRIFLUOR-1-ISOPROPYL-2-OXOPROPYL]-L-PROLINAMIDE

HRID 2393812Notes

Reaction equation

HRID 2393812 reaction equation
CCCCCC.[CH3:7][O:8][C:9]([NH:11][C@@H:12]([CH:33]([CH3:35])[CH3:34])[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:22][CH:23]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH:24]([CH3:26])[CH3:25])=[O:21])=[O:14])=[O:10]>COC(C)(C)C>[CH3:7][O:8][C:9]([NH:11][C@@H:12]([CH:33]([CH3:35])[CH3:34])[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:22][C@H:23]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH:24]([CH3:26])[CH3:25])=[O:21])=[O:14])=[O:10]

Participants

4

Reactant 2

HCID 8058HexaneHCID 11796530HCID 11796530, compound

Product 1

HCID 9910174N''-[N-METHOXYCARBONYL-L-VALYL]-N-[(S)-3,3,3-TRIFLUOR-1-ISOPROPYL-2-OXOPROPYL]-L-PROLINAMIDEYield 30%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Hexane (13 ml) was added to a solution of (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoroacetyl)propyl]pyrrolidine-2-carboxamide (0.85 g; SSS:SSR 53:47; hydrate:ketone 1:1) in tert-butyl methyl ether (8.5 ml) until cloudiness persisted. The solution was then warmed to give a clear solution, seeded with substantially pure crystalline SSS diastereoisomer and allowed to stand. A white solid crystallised which was collected by filtration to give (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[(S)-2-methyl-1-(2,2,2-trifluoroacetyl)propyl]-pyrrolidine-2-carboxamide as a crystalline solid in 30% yield, SSS:SSR 95:5; hydrate:ketone 80:20; NMR similar to that of the product of Example 2.

Workup

  1. temperatureThe solution was then warmed
  2. customto give a clear solution
  3. customA white solid crystallised which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e9718dae239d40febe6b90d981e4aca4
Source dataset
uspto-grants-1998_09
Patent number
US05808097

Reaction notes

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