5,5-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione → (1S,2S,5R,6S)-2-Amino-2-(3'-chlorobenzyloxycarbonyl)-bicyclo [3.1.0]hexane-6-carboxylic acid

HRID 1823647Notes

Reaction equation

HRID 1823647 reaction equation
C(OC([NH:7][C@@:8]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:18])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:14]([OH:16])=[O:15])=O)C=C.CC1(C)C(=O)NC(=O)NC1=O>>[NH2:7][C@@:8]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:18])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 905095,5-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneHCID 23569528(1S,2S,5R,6S)-2-Allyloxycarbonylamino-2-(3'-chloro-benzyloxycarbonyl)-bicyclo [3.1.0]hexane-6-carboxylic acid

Product 1

HCID 10286782(1S,2S,5R,6S)-2-Amino-2-(3'-chlorobenzyloxycarbonyl)-bicyclo [3.1.0]hexane-6-carboxylic acid

Procedure

(1S,2S,5R,6S)-2-Allyloxycarbonylamino-2-(3′-chloro-benzyloxycarbonyl)-bicyclo[3.1.0]hexane-6-carboxylic acid (708 mg, 1.8 mmol) was reacted with dimethylbarbituric acid (421 mg, 2.7 mmol) and tetrakis triphenylphosphine palladium (0) (42 mg; 0.02 mmol) under general procedure 4. The title compound was obtained as a white solid (385 mg, 62% yield).

Sources & evidence

ORD record
ord-20f4113af7884daca775c85202a1fd44
Source dataset
uspto-grants-2006_05
Patent number
US07038077B2

Reaction notes

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