Trifluoroacetic acid → 1,2-dimethyl-L-prolyl-N-[(2R,3S,4S)-1-carboxy-2-methoxy-4-methylhexan-3-yl]-N-methyl-L-valinamide

HRID 74812Notes

Reaction equation

HRID 74812 reaction equation
[CH3:1][N:2]1[CH2:33][CH2:32][CH2:31][C@@:3]1([CH3:34])[C:4]([NH:6][C@H:7]([C:11]([N:13]([C@@H:15]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C@H:16]([O:25][CH3:26])[CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH3:14])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[CH2:33][CH2:32][CH2:31][C@@:3]1([CH3:34])[C:4]([NH:6][C@H:7]([C:11]([N:13]([C@@H:15]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[C@H:16]([O:25][CH3:26])[CH2:17][C:18]([OH:20])=[O:19])[CH3:14])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866857661,2-dimethyl-L-prolyl-N-[(3R,4S,5S)-1-tert-butoxy-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Product 1

HCID 866857671,2-dimethyl-L-prolyl-N-[(2R,3S,4S)-1-carboxy-2-methoxy-4-methylhexan-3-yl]-N-methyl-L-valinamideYield 152%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure B, from #202 (5.2 g, 10.77 mmol, 1 eq.), dichloromethane (45 mL), and trifluoroacetic acid (20 mL) was synthesized the crude desired material, to obtain #203 (7 g, quantitative yield) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-75081219c3b841b2be744eac57988196
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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