(6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid → (S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid

HRID 10992Notes

Reaction equation

HRID 10992 reaction equation
[CH2:1]([C@H:4]1[C:8]2=[N:9][CH:10]=[C:11]([N:14]([CH2:25][CH:26]=[CH2:27])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:12](=[O:13])[N:7]2[C@H:6]([C:28]([OH:30])=[O:29])[CH2:5]1)[CH:2]=[CH2:3].[CH2:31](N(C1C(=O)N2[C@H](C(N(C(OC(C)(C)C)=O)C3C=CC=CC=3)=O)CC(CC=C)(CC=C)C2=NC=1)C(=O)OCC1C=CC=CC=1)[CH:32]=[CH2:33]>>[CH2:1]([C:4]1([CH2:33][CH:32]=[CH2:31])[C:8]2=[N:9][CH:10]=[C:11]([N:14]([CH2:25][CH:26]=[CH2:27])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:12](=[O:13])[N:7]2[C@H:6]([C:28]([OH:30])=[O:29])[CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 57444828(6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic AcidHCID 86590675benzyl (S)-allyl-[8,8-diallyl-6-(tert-butoxycarbonyl-phenyl-aminocarbonyl)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl]-carbamate

Product 1

HCID 57444829(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic AcidYield 76%

Procedure

According to the procedure for the preparation of 28d, 29c (372 mg, 0.595 mmol) afforded 202 mg (76%) of 29d. MS (ESI) 450.4 (M+H+), 448.2 (M−H+).

Sources & evidence

ORD record
ord-dfdbf4c619de41a5b993938d44077dc6
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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