Sodium Bicarbonate → HCID 69736562, compound

HRID 481098Notes

Reaction equation

HRID 481098 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) δ7.8 (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.

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-8f8a85add7af427e818e007ed26d9607
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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