Triethylamine → N1-(2-Hydroxy-3,3,3-trifluoro-1-isopropylpropyl) N2-phenylmethyloxycarbonyl-prolinamide

HRID 1440046Notes

Reaction equation

HRID 1440046 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:18][CH2:17][CH2:16][C@H:12]2[C:13](O)=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:20][CH:21]([CH:28]([CH3:30])[CH3:29])[CH:22]([OH:27])[C:23]([F:26])([F:25])[F:24].C(N(CC)CC)C.[OH:38]S([O-])(=O)=O.[K+]>C(Cl)Cl>[OH:27][CH:22]([C:23]([F:24])([F:25])[F:26])[CH:21]([N:20]1[CH2:13][CH2:12][CH2:16][C@H:17]1[C:18]([NH:11][C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10])=[O:38])[CH:28]([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 516920Potassium bisulfateHCID 14503247HCID 14503247, compound

Product 1

HCID 57181026N1-(2-Hydroxy-3,3,3-trifluoro-1-isopropylpropyl) N2-phenylmethyloxycarbonyl-prolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 1.1 g of N-phenylmethyloxycarbonyl proline TDO-ester (Cf Hollitzer, Seewald and Steglichm Ang. Int. Edit. 1976, Vol. 15, 444) and 0.42 g of 3-amino-1,1,1-trifluoro-4-methyl-2-pentanol hydrochloride in 50 ml of CH2Cl2 was added dropwise 0.40 g of triethylamine. After stirring for 14 hours at 25° C., aqueous KHSO4 was added, the layers separated and the organic layer washed with aqueous KHSO4, aqueous KHCO3, H2O and then brine (2x). After drying (MgSO4), solvents were flash evaporated to yield 0.54 g of a solid residue which was recrystallized in Et20 to give 0.24 g of the analytically pure expected amide; m.p. 99° C.

Workup

  1. customthe layers separated
  2. washthe organic layer washed with aqueous KHSO4, aqueous KHCO3, H2O
  3. dry with materialAfter drying (MgSO4), solvents
  4. customevaporated

Sources & evidence

ORD record
ord-5a866d81b8b4475ebba791fa854ac4e5
Source dataset
uspto-grants-1996_03
Patent number
US05496927

Reaction notes

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