Sodium Bicarbonate → HCID 66603654, compound

HRID 80480Notes

Reaction equation

HRID 80480 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[NH2:18][C:19]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH3:36][C:34]([CH3:37])([O:33][C:31]([NH:30][CH2:29][C:26]1[CH:27]=[CH:28][C:19]([NH:18][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]2)=[C:20]([C:21]([O:23][CH3:24])=[O:22])[CH:25]=1)=[O:32])[CH3:35]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 643496Benzyl 4-oxopiperidine-1-carboxylate2×HCID 5049666Sodium triacetoxyborohydride2×HCID 60103040Methyl 2-amino-5-((((tert-butoxy)carbonyl)amino)methyl)benzoate

Product 1

HCID 66603654HCID 66603654, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.66 g of benzyl 4-oxopiperidine-1-carboxylate and 1 g of methyl 2-amino-5-({[(1,1-dimethylethoxy)carbonyl]amino}methyl)benzoate obtained in stage 5.1 in 20 ml of DCM is added dropwise at AT to a suspension of 2.04 g of NaBH(OAc)3 in a mixture of 20 ml of DCM and 0.41 ml of AcOH. The mixture is stirred at AT for 15 h 00 and then a further 2.04 g of NaBH(OAc)3 are added. After stirring for 6 h 00, 1.66 g of benzyl 4-oxopiperidine-1-carboxylate are added and the mixture is stirred at AT for 48 h 00. A saturated NaHCO3 solution is added and extraction is carried out with DCM. The organic phase is washed with a saturated NaHCO3 solution and twice with a saturated NH4Cl solution. It is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (5/95, v/v) as far as (40/60, v/v), to give 1.6 g of the expected product.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at AT for 48 h 00
  3. extractionextraction
  4. washThe organic phase is washed with a saturated NaHCO3 solution and twice with a saturated NH4Cl solution
  5. dry with materialIt is dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-c9c1cc450d3d4ff4abec96d79b800fb1
Source dataset
uspto-grants-2014_09
Patent number
US08846654B2

Reaction notes

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