Dimethylbarbituric acid → HCID 66628105, compound

HRID 1665894Notes

Reaction equation

CN1C(=O)CC(=O)N(C)C1=O.[CH2:12]([O:14][C:15]([C@:17]1([F:47])[C@@H:22]2[C@H:18]1[CH2:19][C@@H:20]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=1)[C@@:21]2([NH:30]C(OCC=C)=O)[C:23]([O:25][CH:26]([CH2:28][CH3:29])[CH3:27])=[O:24])=[O:16])[CH3:13]>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:12]([O:14][C:15]([C@:17]1([F:47])[C@@H:22]2[C@H:18]1[CH2:19][C@@H:20]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([Cl:46])[CH:40]=1)[C@@:21]2([NH2:30])[C:23]([O:25][CH:26]([CH2:28][CH3:29])[CH3:27])=[O:24])=[O:16])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

81 mg of 1,3-dimethylbarbituric acid and 12 mg of tetrakis(triphenylphosphine) palladium were added to 190 mg of (1R,2R,3R,5R,6R)-2-allyloxycarbonylamino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-butyl ester 6-ethyl ester dissolved in chloroform under a nitrogen atmosphere, and the mixture was stirred for 1 hour at 50° C. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (silica gel: Kanto Chemical silica gel 60 (spherical), eluent: hexane-ethyl acetate=5:1), thereby yielding 180 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-butyl ester 6-ethyl ester.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe obtained residue was purified by column chromatography (silica gel: Kanto Chemical silica gel 60 (spherical), eluent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record: ord-fa3deb984a3a45c0857ed4cbc80b7953
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039647B2

Reaction notes

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