Diisopropylethylamine → HCID 67410996, compound

HRID 1949650Notes

Reaction equation

[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:49][C:50]1[CH:58]=[C:57]2[C:53]([C:54]([CH:59]3[CH2:63][N:62]([C:64]4[N:69]=[CH:68][CH:67]=[CH:66][N:65]=4)[CH:61]4[CH2:70][CH2:71][NH:72][CH:60]34)=[CH:55][NH:56]2)=[CH:52][CH:51]=1>CN1C(=O)CCC1.C(OCC)C>[C:12]([O:11][C:9](=[O:10])[NH:1][CH:2]([C:6]([N:72]1[CH2:71][CH2:70][CH:61]2[N:62]([C:64]3[N:69]=[CH:68][CH:67]=[CH:66][N:65]=3)[CH2:63][CH:59]([C:54]3[C:53]4[C:57](=[CH:58][C:50]([F:49])=[CH:51][CH:52]=4)[NH:56][CH:55]=3)[CH:60]12)=[O:8])[CH:3]([CH3:4])[CH3:5])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution containing Boc-Val-OH (106 mg, 0.48 mmol) in anhydrous NMP (3 mL) was cooled to 0° C. HATU (185 mg, 0.48 mmol) and DIPEA (67 mg, 0.52 mmol) were added followed by the addition of crude 71 (150 mg, 0.46 mmol) in anhydrous NMP (3 mL). After 2.5 h, the reaction mixture was diluted with diethyl ether and washed successively with water, aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 210 mg (86%) of 72 as a white-colored foam. Mass spectrum, m/z [523] (M+H)+.

Workup

washwashed successively with water, aqueous NaHCO3, water, and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-f579f401acc3474da5ce7c7210ae8d7c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399683B2

Reaction notes

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