Phenyl chloroformate → HCID 23122081, compound

HRID 1713530Notes

Reaction equation

HRID 1713530 reaction equation
[CH:1]1([C:7]2([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[C:32](Cl)(=[O:40])[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[CH:17]1([C:7]2([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:11]3[CH2:12][N:13]([C:32]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:40])[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 23121933HCID 23121933, compound

Product 1

HCID 23122081HCID 23122081, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dicyclohexyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.13 g, 0.42 mmol) in tetrahydrofuran (1 mL) were sequentially added diisopropylethylamine (0.5 mL) and phenyl chlorocarbonate (0.10 g, 0.64 mmol), and the mixture was stirred at room temperature for 14 hours. The reaction solution was concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3), crystallized from diisopropyl ether and dried to obtain the title compound (88 mg, yield 49%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3)
  3. customcrystallized from diisopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-10ead6ba4333415cbfe51b709b6ccf9b
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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