Trifluoroacetic acid → Auristatin F hydroxypropylamide L-Alanine

HRID 2405553Notes

Reaction equation

[CH3:1][CH2:2][C@@H:3]([C@H:5]([N:36]([C:38]([C@@H:40]([NH:44][C:45]([C@@H:47]([N:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])=[O:46])[CH:41]([CH3:43])[CH3:42])=[O:39])[CH3:37])[C@H:6]([O:34][CH3:35])[CH2:7][C:8]([N:10]1[C@H:14]([C@H:15]([O:32][CH3:33])[C@H:16]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])[CH3:17])[CH2:13][CH2:12][CH2:11]1)=[O:9])[CH3:4].C([NH:61][C@H:62]([C:64]([OH:66])=[O:65])[CH3:63])(OC(C)(C)C)=O.[OH:67][CH2:68][CH2:69][CH2:70][NH-:71].FC(F)(F)C(O)=O>ClCCl>[CH3:1][CH2:2][C@@H:3]([C@H:5]([N:36]([C:38]([C@@H:40]([NH:44][C:45]([C@@H:47]([N:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])=[O:46])[CH:41]([CH3:43])[CH3:42])=[O:39])[CH3:37])[C@H:6]([O:34][CH3:35])[CH2:7][C:8]([N:10]1[C@H:14]([C@H:15]([O:32][CH3:33])[C@H:16]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])[CH3:17])[CH2:13][CH2:12][CH2:11]1)=[O:9])[CH3:4].[OH:67][CH2:68][CH2:69][CH2:70][NH-:71].[NH2:61][C@H:62]([C:64]([OH:66])=[O:65])[CH3:63]

Participants

Conditions

Temperature: 23 °C

Procedure

Auristatin F-hydroxypropylamide Boc-L-Alanine (112 mg, 0.115 mmol, prepared as described in Example 49) was taken up in dichloromethane (3 mL) and excess trifluoroacetic acid was added. The mixture was stirred at 23° C. for 1 hour and the solvent removed under high vacuum. The resulting oil was taken up in dichloromethane (1.5 mL) and precipitation from diethyl ether (30 mL to give the title compound as white solid (96.2 mg, 85%).

Workup

customthe solvent removed under high vacuum
customprecipitation from diethyl ether (30 mL

Sources & evidence

ORD record: ord-2888c664eae44ba2b6cc78af10e8af13
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08808679B2

Reaction notes

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