Trifluoroacetic acid → N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-(adamantan-1-ylmethoxy)-1-oxo-3-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide trifluoro acetate

HRID 882585Notes

Reaction equation

HRID 882585 reaction equation
C(O[C:6]([N:8](C)[C@H:9]([C:13]([NH:15][C@H:16]([C:20]([N:22]([C@@H:24]([C@@H:66]([CH3:69])[CH2:67][CH3:68])[C@H:25]([O:64][CH3:65])[CH2:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C@H:34]([O:62][CH3:63])[C@@H:35]([CH3:61])[C:36]([NH:38][C@@H:39]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:40]([O:42][CH2:43][C:44]12[CH2:53][CH:48]3[CH2:49][CH:50]([CH2:52][CH:46]([CH2:47]3)[CH2:45]1)[CH2:51]2)=[O:41])=[O:37])=[O:28])[CH3:23])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[C:71]([OH:77])([C:73]([F:76])([F:75])[F:74])=[O:72]>ClCCl>[F:74][C:73]([F:76])([F:75])[C:71]([OH:77])=[O:72].[CH3:6][NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:20]([N:22]([C@@H:24]([C@@H:66]([CH3:69])[CH2:67][CH3:68])[C@H:25]([O:64][CH3:65])[CH2:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C@H:34]([O:62][CH3:63])[C@@H:35]([CH3:61])[C:36]([NH:38][C@@H:39]([CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:40]([O:42][CH2:43][C:44]12[CH2:45][CH:46]3[CH2:52][CH:50]([CH2:49][CH:48]([CH2:47]3)[CH2:53]1)[CH2:51]2)=[O:41])=[O:37])=[O:28])[CH3:23])=[O:21])[CH:17]([CH3:18])[CH3:19])=[O:14])[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86678344N-(tert-butoxycarbonyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2 S)-1-(adamantan-1-ylmethoxy)-1-oxo-3-phenylpropan-2-yl]amino)-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Product 1

HCID 86678342N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-(adamantan-1-ylmethoxy)-1-oxo-3-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide trifluoro acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27.5 mg (28 μmol) of N-(tert-butoxycarbonyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(2S)-1-(adamantan-1-ylmethoxy)-1-oxo-3-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide were dissolved in 1.8 ml of dichloromethane, and 361 μl of TFA were added. The reaction mixture was stirred for 30 min and then concentrated. The residue was taken up in water and lyophilized. 22.7 mg (81% of theory) of the title compound were obtained.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-6a7bd13c080142899b02f2e384920acd
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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