Triethylamine → (R)-Benzyloxycarbonylamino-indan-2-yl-acetic acid

HRID 220072Notes

Reaction equation

HRID 220072 reaction equation
[NH2:1][C@H:2]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH2:22]([O:29][C:30](ON1C(=O)CCC1=O)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCOCC1.O>[CH2:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:6]1[C@@H:2]([NH:1][C:30]([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 12192007(R)-2-Amino-2-(2,3-dihydro-1H-inden-2-yl)acetic acid

Product 1

HCID 11631222(R)-Benzyloxycarbonylamino-indan-2-yl-acetic acidYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

(2R)-amino(2,3-dihydro-1H-inden-2-yl)ethanoic acid (1.91 g, 10 mmol) was suspended in dioxane (10 ml) and water (10 ml). To this was added triethylamine (1.7 ml) and N-(benzyloxycarbonyloxy)-succinimide (2.54 g) and the reaction mixture was stirred rapidly at room temperature for 2 days. The reaction mixture was poured into water (50 ml) and extracted with chloroform (100 ml). The organic phase was washed with 1N hydrochloric acid (50 ml) and water (50 ml). This was dried over magnesium sulphate and the solvent removed in vacuo to give the title compound (3.06 g, 94%):

Workup

  1. extractionextracted with chloroform (100 ml)
  2. washThe organic phase was washed with 1N hydrochloric acid (50 ml) and water (50 ml)
  3. dry with materialThis was dried over magnesium sulphate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4ead24af4e3d4b658623534790323066
Source dataset
uspto-grants-2012_06
Patent number
US08202864B2

Reaction notes

Loading…