Sodium Bicarbonate → HCID 69736562, compound

HRID 497416Notes

Reaction equation

HRID 497416 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([O:23][CH3:24])[N:17]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].[C:26](=[O:29])(O)[O-:27].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([C:16]1[C:21]([NH:22][C:26]([O:27][CH2:15][C:12]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)=[O:29])=[CH:20][CH:19]=[C:18]([O:23][CH3:24])[N:17]=1)[S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69736451HCID 69736451, compound

Product 1

HCID 69736562HCID 69736562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.45 g (0.026 m) of [3-amino-6-methoxy-pyridin-2-yl]-[toluene-4-sulfonyl]-acetic acid ethyl ester dissolved in 150 mL of methylene chloride is added 150 mL of saturated sodium bicarbonate followed by 5.56 mL (0.038 m) of carbo-benzyloxy chloride. The reaction mixture is stirred for 20 hours at room temperature. The water layer is separated from the organic layer and the organic layer is dried (Na2SO4) and evaporated to yield 15.73 grams of [3-benzyloxycarbonylamino-6-methoxy-pyridin-2-yl]-[toluene-4-sulfonyl]-acetic acid ethyl ester as a yellow solid. 1H NMR (CDCl3) δ 7.8 (m, 1H), 7.6 (m, 1H), 7.3 (m, 10H), 6.7 (m, 1H), 5.2 (m, 3H), 4.0 (m, 2H), 3.3 (s, 3H), 3.1 (m, 2H), 1.1 (m, 3H). TLC (7/3 hexanes/ethyl acetate) Rf=0.6. Step 5:

Workup

  1. customThe water layer is separated from the organic layer
  2. dry with materialthe organic layer is dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-1359c9ed922b446197703fbe9bbb5148
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

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