Tributylphosphine → benzyl {(3R,4R)-4-methyl-1-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamate

HRID 1434525Notes

Reaction equation

HRID 1434525 reaction equation
O[CH2:2][C@H:3]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:4]([C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C:15]2=[O:20])=[C:10]([CH3:21])[CH:9]=1)[CH3:5].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:5][C@H:4]1[C:6](=[O:22])[N:7]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C:15]3=[O:20])=[C:10]([CH3:21])[CH:9]=2)[CH2:2][C@@H:3]1[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 86605956benzyl {(1R,2R)-1-hydroxymethyl-2-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-propyl}-carbamate

Product 1

HCID 86605957benzyl {(3R,4R)-4-methyl-1-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenyl]-5-oxo-pyrrolidin-3-yl}-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 2c from benzyl {(1R,2R)-1-hydroxymethyl-2-[3-methyl-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-propyl}-carbamate with di-tert.-butyl azodicarboxylate and tributylphosphine in THF and subsequent purification by reversed-phase chromatography.

Sources & evidence

ORD record
ord-0a8b5168102c47c7adf0da2c5e930809
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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