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

HRID 366924Notes

Reaction equation

HRID 366924 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 (2×). After drying (MgSO4), solvents were flash evaporated to yield 0.54 g of a solid residue which was recrystallized in Et2O 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-b1b9eb762f024a81a9ff5d31a35c1183
Source dataset
uspto-grants-2000_10
Patent number
US06130315

Reaction notes

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