Phenylmethyl ({[({[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl)oxy]carbonyl}oxy)acetate → ({[({[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl)oxy]carbonyl}oxy)acetic acid

HRID 1430726Notes

Reaction equation

HRID 1430726 reaction equation
C1(C[O:8][C:9](=[O:45])[CH2:10][O:11][C:12]([O:14][CH2:15][O:16][C:17]2[C:18](=[O:44])[C:19]([C:32]([NH:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=3[F:43])=[O:33])=[CH:20][N:21]3[C:26]=2[C:25](=[O:27])[N:24]2[C@@H:28]([CH3:31])[CH2:29][O:30][C@@H:23]2[CH2:22]3)=[O:13])C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.CO>[F:43][C:37]1[CH:38]=[C:39]([F:42])[CH:40]=[CH:41][C:36]=1[CH2:35][NH:34][C:32]([C:19]1[C:18](=[O:44])[C:17]([O:16][CH2:15][O:14][C:12]([O:11][CH2:10][C:9]([OH:45])=[O:8])=[O:13])=[C:26]2[C:25](=[O:27])[N:24]3[C@@H:28]([CH3:31])[CH2:29][O:30][C@@H:23]3[CH2:22][N:21]2[CH:20]=1)=[O:33]

Participants

5

Reactant 2

HCID 44626148Phenylmethyl ({[({[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl)oxy]carbonyl}oxy)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 44626082({[({[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl)oxy]carbonyl}oxy)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Phenylmethyl({[({[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl)oxy]carbonyl}oxy)acetate (prepared as described in example 17) (247 mg, 0.394 mmol) 10 w.t. % palladium on carbon (190 mg) were stirred in an ethyl acetate/methanol mixture under 1 atm hydrogen atmosphere for 30 minutes. The reaction was filtered through celite and concentrated under reduced pressure to yield a white solid. 1H NMR (CDCl3) δ 10.28 (m, 1H), 8.32 (s, 1H), 7.28 (m, 1H), 6.76 (m, 2H), 5.92 (d, J=6.4 Hz, 1H), 5.86 (d, J=6.4 Hz, 1H), 5.28 (dd, J=10, 3.2 Hz, 1H), 4.55 (br s, 4H), 4.37-4.28 (m, 3H), 3.91 (m, 1H), 3.63 (m, 1H), 3.35 (m, 1H), 1.34 (d, J=6 Hz, 3H). ES+ MS: 538 (M+1).

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customto yield a white solid

Sources & evidence

ORD record
ord-a362c66c19d54a748429c8d661e59c51
Source dataset
uspto-grants-2015_01
Patent number
US08940912B2

Reaction notes

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