1-Hydroxybenzotriazole → HCID 68609646, compound

HRID 14175Notes

Reaction equation

[ClH:1].[CH2:2]([N:5]([CH2:15][CH2:16][CH3:17])[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][N:14]=1)[C:9]([OH:11])=O)[CH2:3][CH3:4].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:52][C@@H:53]([CH2:67][C:68]1[CH:73]=[C:72]([F:74])[CH:71]=[C:70]([F:75])[CH:69]=1)[C@H:54]([OH:66])[CH2:55][NH:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([CH2:64][CH3:65])[CH:59]=1>C(Cl)Cl.C(N(CC)CC)C>[ClH:1].[F:74][C:72]1[CH:73]=[C:68]([CH:69]=[C:70]([F:75])[CH:71]=1)[CH2:67][C@H:53]([NH:52][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][N:14]=[C:6]([N:5]([CH2:2][CH2:3][CH3:4])[CH2:15][CH2:16][CH3:17])[CH:7]=1)[C@H:54]([OH:66])[CH2:55][NH:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[C:60]([CH2:64][CH3:65])[CH:59]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 2-(Dipropylamino)isonicotinic acid hydrochloride (0.2 g) in methylene chloride (15 mL) was added triethylamine (0.195 g), HOBT (0.105 g), and HATU (0.293 g). The mixture was stirred at 39° C. for 10 minutes at which time (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.285 g) was added. The mixture was stirred at 40° C. for 4 h then poured into methylene chloride (50 mL), washed with water then brine, dried over anhydrous magnesium sulfate and concentrated under vacuum. Column chromatography on silica gel (100 mL) using 5% methanol in methylene chloride as eluent and conversion to the hydrochloride salt gave 0.105 g of the title compound: MS (ESI+) for C31H40F2N4O2 m/z 539.3 (M+H)+.

Workup

additionwas added
washwashed with water
dry with materialbrine, dried over anhydrous magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-fc84939db08c41d2bb94279cd839a3e4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727997B2

Reaction notes

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