HCID 178472450, compound → HCID 178475068, compound

HRID 1087973Notes

Reaction equation

HRID 1087973 reaction equation
[C:1]([NH:4][C@H:5]([C:21]([CH:23]([NH2:48])[CH:24]([CH2:28][C:29]1([C:34](=[O:47])[NH:35][C@H:36]2[CH2:41][CH2:40][C@@H:39]([C:42]([O:44]CC)=[O:43])[CH2:38][CH2:37]2)[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:25]([OH:27])=[O:26])=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=[O:3])[CH3:2]>[OH-].[Na+]>[C:1]([NH:4][C@H:5]([C:21]([CH:23]([NH2:48])[CH:24]([CH2:28][C:29]1([C:34](=[O:47])[NH:35][C@H:36]2[CH2:41][CH2:40][C@@H:39]([C:42]([OH:44])=[O:43])[CH2:38][CH2:37]2)[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:25]([OH:27])=[O:26])=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 178472450HCID 178472450, compound

Product 1

HCID 178475068HCID 178475068, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ethyl ester from Example 39 (404 mg, 0.600 mmol) was dissolved in 2M sodium hydroxide solution (10 ml), and the resulting solution was kept at room temperature overnight. The reaction mixture was diluted to 30 ml and extracted with diethyl ether. The aqueous phase was acidified to pH 1 with 2M hydrochloric acid and extracted with ethyl acetate (3×25 ml). The organic phase was dried (MgSO4) and evaporated to afford the title compound (375 mg, 97%) as a white foam. Found: C,58.30; H,7.24; N,8.20. C33H48N4O9. (0.25 CH2Cl2, 1.25 H2O) requires C,58.00; H,7.17; N,8.14%.

Workup

  1. additionThe reaction mixture was diluted to 30 ml
  2. extractionextracted with diethyl ether
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f11260aa197144b585773a70ed61a373
Source dataset
uspto-grants-1990_10
Patent number
US04960792

Reaction notes

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