Diisopropylethylamine → HCID 68703426, compound

HRID 1437381Notes

Reaction equation

HRID 1437381 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]([C@@H:9]1[CH2:14][CH2:13][C@@H:12]([NH2:15])[C@H:11]([OH:16])[CH2:10]1)=[O:8].[C:17](=O)([O:23]C(C)(C)C)[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:5][O:6][C:7]([C@@H:9]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:23])[C@H:11]([OH:16])[CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 68699181HCID 68699181, compound

Product 1

HCID 68703426HCID 68703426, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The acetate salt (c) (15.6 g, 66 mmol) was suspended in tetrahydrofuran (200 ml) and treated with di-tert-butyl carbonate (16 g, 73 mmol) and diisopropylethylamine (14 ml, 10.4 g, 80 mmol). The mixture was heated at 50° C. for 18 hours then evaporated to dryness. The residue was partitioned between water and ethyl acetate. The aqueous phase was further extracted with ethyl acetate and the combined extracts washed with brine, dried and evaporated to give a solid (18.5 g, 100%).

Workup

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was further extracted with ethyl acetate
  4. washthe combined extracts washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-baf3771c42d0430e98832f5c23d3e5a6
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

Loading…