Triphenylphosphine → HCID 59596700, compound

HRID 2264801Notes

Reaction equation

C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH2:34][C:35]([C@@H:37]1[CH2:41][CH2:40][C@H:39]([C:42]2[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=2)[N:38]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:36].[C:56]1([C@H:62](O)[CH3:63])[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C1COCC1>[NH2:34][C:35]([C@@H:37]1[CH2:41][CH2:40][C@H:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48][C@@H:62]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH3:63])=[CH:44][CH:43]=2)[N:38]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

Polystyrene supported PPh3 (100 mg, 1.5 mmol) and DIAD (30 mg, 1.5 mmol) were added to a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-1-pyrrolidinecarboxylate (D13, 30 mg, 0.10 mmol) in dry THF (1 ml) at 0° C. After 15 min (1R)-1-phenylethanol (24.4 mg, 0.2 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The resin was filtered off and the solvent was evaporated. The crude material was purified by chromatography on silica gel using cyclohexanes/ethyl acetate (8:2) to afford the title compound (20 mg, 48%); Rt (HPLC): 5.70 min, 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 1.31 (s, 9H); 1.53 (d, 3H); 1.65-1.78 (m, 1H); 1.79-1.92 (m, 1H); 1.93-2.03 (m, 1H); 2.07-2.21 (m, 1H); 4.50 (br. s., 1H); 4.70 (br. s., 1H); 5.41-5.50 (m, 1H); 6.78 (d, 2H); 6.91 (s, 1H); 7.23 (br. s., 1H); 7.31 (br. s., 2H); 7.39 (br. s., 4H); 7.44 (br. s., 1H).

Workup

filtrationThe resin was filtered off
customthe solvent was evaporated
customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-c5b5eb2cbd4d4981af6031b500400d95
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855218B2

Reaction notes

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