tert-Butyl (4,4-dimethyl-1-oxopentan-3-yl)carbamate → HCID 86670143, compound

HRID 1631759Notes

Reaction equation

HRID 1631759 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.[CH3:16][C:17]([CH3:31])([CH3:30])[CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:19][CH:20]=O>[Na].C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:20][CH2:19][CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]([CH3:16])([CH3:30])[CH3:31])[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 17039462tert-Butyl (4,4-dimethyl-1-oxopentan-3-yl)carbamateHCID 86670088(R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 86670143HCID 86670143, 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, 115 mg, 0.507 mmol), tert-butyl 4,4-dimethyl-1-oxopentan-3-ylcarbamate (116 mg, 0.507 mmol), titanium(IV) chloride in CH2Cl2 (1M, 0.761 mL, 0.761 mmol) and sodium triacetoxyhydroborate (237 mg, 1.116 mmol) in CH2Cl2 (5 mL) (53 mg, 24%). ESI-MS m/z [M+H]+ calc'd for C21H34ClN5O3, 440.24. found 440.4.

Sources & evidence

ORD record
ord-1729a5f2e566415884a24559a92ec969
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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