Carbon Tetrachloride → HCID 59656620, compound

HRID 2054759Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C@H:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)[CH:10]=1.CCN(C(C)C)C(C)C.C(Cl)(Cl)(Cl)Cl.[P:40]([O-:57])([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CC#N.CN(C1C=CN=CC=1)C>[P:40]([O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C@@H:11]2[CH:10]=[C:9]([C:3]3[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=3[F:1])[CH2:13][N:12]2[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:20]=1)([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:57]

Participants

Conditions

Temperature: 25 °C

Procedure

(2S)-4-(2,5-difluorophenyl)-2-(3-hydroxyphenyl)-N,N-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxamide (4-2, 97 mg, 0.28 mmol) in anhydrous CH3CN (1.0 mL) at 0° C. was treated sequentially with iPr2NEt (0.10 mL, 0.6 mmol), CCl4 (0.14 mL, 1.5 mmol), DMAP (catalytic) and lastly dibenzyl phosphite (0.09 mL, 0.40 mmol) and the resulting off-yellow solution was stirred 2 h at 25° C. Upon completion, the reaction was concentrated and directly subjected to flash column chromatography (SiO2, 0-100% EtOAc/hexanes gradient) to provide dibenzyl 3-{(2S)-4-(2,5-difluorophenyl)-1-[(dimethylamino)carbonyl]-2,5-dihydro-1H-pyrrol-2-yl}phenyl phosphate (8-1) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.30 (m, 11H), 7.15 (m, 2H), 7.05 (m, 2H), 6.96 (m, 2H), 6.32 (br s, 1H), 6.10 (m, 1H), 5.12 (d, J=1.8 Hz, 2H), 5.09 (d, J=1.8 Hz, 2H), 4.78 (ddd, J=13.7, 5.8, 1.8 Hz, 1H), 4.47 (d, J=13.7 Hz, 1H), 2.85 (s, 6H). LRMS m/z (M+H) 605.6 found, 605.6 required.

Workup

concentrationUpon completion, the reaction was concentrated

Sources & evidence

ORD record: ord-52ddceff815e4d4bba8fe4c776841c33
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329762B2

Reaction notes

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