Hydrochloric Acid → HCID 57905090, compound

HRID 1093056Notes

Reaction equation

HRID 1093056 reaction equation
[OH:1][C:2]1[C:14](=[O:15])[N:6]2[CH2:7][CH:8]3[CH2:13][CH:12]([C:5]2=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][NH:10][CH2:9]3.C(N(C(C)C)CC)(C)C.[CH2:30]([O:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>C(Cl)Cl>[OH:1][C:2]1[C:14](=[O:15])[N:6]2[CH2:7][CH:8]3[CH2:13][CH:12]([C:5]2=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][N:10]([C:38]([O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:39])[CH2:9]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 57905070HCID 57905070, compound

Product 1

HCID 57905090HCID 57905090, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To ethyl 3-hydroxy-4-oxo-6,7,8,9,10,11-hexahydro-4H-7,11-methanopyrimido[1,2-a][1,5]diazocine-2-carboxylate (0.26 g, 0.661 mmol) in CH2Cl2 (5 mL) was added diisopropylethylamine (0.576 mL, 3.31 mmol) and benzylchloroformate (0.102 mL, 0.727 mmol). The reaction mixture was stirred at 23° C. for 16 hours. HCl (1N, 15 mL) was then added to the reaction mixture and the organic material extracted with CH2Cl2 (3×15 mL) and ethyl acetate (3×15 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The organic material was purified by Silica gel column chromatography (Biotage flash chromatography system) eluting with gradient of ethyl acetate 100% to ethyl acetate methanol (1:9) to afford 0.036 g (13% yield) of the title compound. 1H NMR (400 MHz, MeOD) δ ppm 7.36 (5 H, s), 4.95-5.10 (2 H, m) 3.95-4.40 (2 H, br m), 2.75-3.30 (5 H, br m), 1.75-2.50 (4 H, m), 0.95-1.45 (4 H, m). LCMS (+ESI, M+H+) m/z: 414.

Workup

  1. extractionthe organic material extracted with CH2Cl2 (3×15 mL) and ethyl acetate (3×15 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe organic material was purified by Silica gel column chromatography (Biotage flash chromatography system)
  5. washeluting with gradient of ethyl acetate 100% to ethyl acetate methanol (1:9)

Sources & evidence

ORD record
ord-3c2d7a523f714da9a22dbdae5487ce5e
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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