Sodium Bicarbonate → HCID 22262741, compound

HRID 490008Notes

Reaction equation

HRID 490008 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=2)[N:4]([CH3:30])[C:3]=1[CH:31]=[O:32].Cl.[CH2:34]([NH:36][C:37](=[O:46])[C@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH2:39])[CH3:35].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:34]([NH:36][C:37](=[O:46])[CH:38]([NH:39][C:31]([C:3]1[N:4]([CH3:30])[C:5]2[C:10]([C:2]=1[Cl:1])=[CH:9][C:8]([NH:11][C:12]([C:14]1[C:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:22][CH:21]=3)=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:13])=[CH:7][CH:6]=2)=[O:32])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:35]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68951202HCID 68951202, compoundHCID 86602368HCID 86602368, compound

Product 1

HCID 22262741HCID 22262741, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The product from step (b) (407.5 mg, 0.892 mmol), (S)-N-ethyl-2-phenylglycinamide hydrochloride salt (316.3 mg, 1.47 mmol) and acetic acid (10 drops) were suspended in CH2Cl2 (25 mL), and the reaction mixture was stirred at room temperature for 20 min. NaB(OAc)3H (2.1 eq) was then added, and the reaction mixture was stirred at 50° C. for 5.5 h. Saturated NaHCO3 (8 mL) and CHCl3 (12 mL) were then added, and the organic layer was washed with water (6 mL), and then concentrated in vacuo. The product was purified by flash chromatography using 30:70 of hexane:EtOAc to afford 441.4 mg of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 5.5 h
  2. washthe organic layer was washed with water (6 mL)
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-bfba77740b1a4b98959e4f3fcf0f4bd9
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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