Trifluoroacetic acid → (2R,3R)-3-methoxy-2-methyl-N-[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]-3-[(2S)-pyrrolidin-2-yl]propanamide trifluoroacetate

HRID 882577Notes

Reaction equation

HRID 882577 reaction equation
[CH3:1][O:2][C@@H:3]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1C(OC(C)(C)C)=O)[C@@H:4]([CH3:25])[C:5]([NH:7][C@@:8]1([C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[O:18])[CH2:10][C@@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6].[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>ClCCl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[CH3:1][O:2][C@@H:3]([C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C@@H:4]([CH3:25])[C:5]([NH:7][C@@:8]1([C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[O:18])[CH2:10][C@@H:9]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86678340tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino)-3-oxopropyl]pyrrolidine-1-carboxylate2×

Product 1

HCID 86678338(2R,3R)-3-methoxy-2-methyl-N-[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]-3-[(2S)-pyrrolidin-2-yl]propanamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

617 mg (1.2 mmol) of tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino}-3-oxopropyl]pyrrolidine-1-carboxylate (Intermediate 24) were taken up in 44 ml of dichloromethane, 4.4 ml of trifluoroacetic acid were added and the mixture was stirred at RT for 30 min. Subsequently, the reaction mixture was concentrated under reduced pressure and the remaining residue was lyophilized from dioxane/water. 702 mg (quant.) of the deprotected compound (2R,3R)-3-methoxy-2-methyl-N-[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]-3-[(2S)-pyrrolidin-2-yl]propanamide trifluoroacetate were obtained as a crude product, which was used in the following stage without further purification.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9aa36f137a064532bd2c4b6123ee3e12
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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