Water → HCID 54033323, compound

HRID 2401607Notes

Reaction equation

HRID 2401607 reaction equation
[CH2:1]([N:8]([C:29]1([CH3:38])[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40].O.C(OCC)(=O)C>N1C=CC=CC=1>[CH2:1]([N:8]([C:29]1([CH3:38])[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[CH2:9][C@H:10]([O:11][C:39](=[O:41])[CH3:40])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:14]([N+:26]([O-:28])=[O:27])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 66822916HCID 66822916, compound

Product 1

HCID 54033323HCID 54033323, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)-2-[Benzyl-(2-methyl-indan-2-yl)-amino]-1-(4-benzyloxy-3-nitro-phenyl)-ethanol (2.75 g) is dissolved in pyridine (15 mL). Acetic anhydride (1.66 g) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by TLC after 18 hours. Water (10 mL) is added to quench the reaction. Ethyl acetate (250 mL) is added and the solution is washed with 1M KHSO4 (3×100 mL), saturated NaHCO3 (100 mL), water (100 mL) and brine (100 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The product is not purified further. TLC (silica, n-hexane/ethyl acetate 4:1 Rf=0.40).

Workup

  1. customto quench
  2. customthe reaction
  3. washthe solution is washed with 1M KHSO4 (3×100 mL), saturated NaHCO3 (100 mL), water (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe product is not purified further

Sources & evidence

ORD record
ord-491a713ba00940c4a362688ba11f2c0b
Source dataset
uspto-grants-2014_08
Patent number
US08796307B2

Reaction notes

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