Sodium Bicarbonate → HCID 60918309, compound

HRID 1364561Notes

Reaction equation

HRID 1364561 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1)=O.Cl.[CH3:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[NH2:8][CH2:7][C:6]1[CH:16]=[CH:17][C:3]([CH2:1][NH:27][C:26]2[CH:28]=[CH:29][C:23]([S:20]([CH3:19])(=[O:21])=[O:22])=[CH:24][CH:25]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 60918309HCID 60918309, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of tert-butyl N-(4-formylbenzyl)carbamate (45 mg, 0.2 mmol) and 4-methanesulfonylaniline hydrochloride (41 mg, 0.2 mmol) in 1 mL of methanol was stirred at room temperature for 30 min, then 0.15 mL of acetic acid was added, followed by 16 mg (0.24 mmol) of sodium cyanoborohydride. The reaction was complete in 5 h. The mixture was treated with saturated sodium bicarbonate solution until pH=8, then extracted with ethyl acetate twice. The combined organics were dried over MgSO4, filtered, and concentrated. The solid was dissolved in 1 mL of methylene chloride, followed by the addition of 0.1 mL of trifluoroacetic acid. The mixture was stirred at room temperature overnight, then concentrated to afford the titled compound as an oil.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe solid was dissolved in 1 mL of methylene chloride
  6. additionfollowed by the addition of 0.1 mL of trifluoroacetic acid
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-315dc8f7ac894a55ba41ff551a00da0b
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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