Methyl 4-oxobutyrate → HCID 86670134, compound

HRID 2169592Notes

Reaction equation

HRID 2169592 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.O=[CH:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]>[Na].C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:7][C@@H:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 2

HCID 83779Methyl 4-oxobutyrateHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670134HCID 86670134, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 5360545SodiumSolvent

Procedure

The title compound was prepared in a manner similar to PREPARATION x63 using (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 250 mg, 1.103 mmol), methyl 4-oxobutanoate (128 mg, 1.103 mmol), titanium(IV) chloride in CH2Cl2 (1M, 1.654 mL, 1.654 mmol) and sodium triacetoxyhydroborate (514 mg, 2.427 mmol) in CH2Cl2 (8 mL) (164 mg, 46%). ESI-MS m/z [M+H]+ calc'd for C14H19ClN4O3, 327.12; found 327.2.

Sources & evidence

ORD record
ord-9c2187aef6cd4fc0ae4291effd5a931f
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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