Acetic Anhydride → HCID 44464422, compound

HRID 1698447Notes

Reaction equation

HRID 1698447 reaction equation
[C:1]([NH:11][C@@H:12]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:13]([OH:27])[CH:14](CC1C2C(=CC=CC=2)C=CC=1)[NH2:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N([CH2:40][CH3:41])CC)C.C(O[C:46](=[O:48])[CH3:47])(=O)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]([NH:11][C@@H:12]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C@H:13]([OH:27])[CH2:14][N:15]([CH2:9][C:10]1[C:40]2[C:41](=[CH:28][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][CH:5]=1)[C:46](=[O:48])[CH3:47])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86635879HCID 86635879, compound

Product 1

HCID 44464422HCID 44464422, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The Cbz protected amino alcohol (XVII) (0.035 g, 0.076 mmol) was dissolved in 1 ml of anhydrous THF. To this triethylamine (0.11 mmol) was added dropwise. After 10 minutes acetic anhydride (0.11 mmol) was added and 1 mg of DMAP was added. The reaction mixture was stirred for 12 hrs and it was then washed with water. The organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure. It was then subjected to silca gel chromatography with 2:1 hexane/ethyl acetate as eluent to give the acetylated amino alcohol (XVIII) as an oil. 0.028 g (73%). 1H NMR (500 MHz, CDCl3) δ 7.80-8.06 (m, 2H), 7.13-7.49 (m, 15H), 5.02-5.37 (m, 3H), 4.52-4.87 (m, 2H), 3.75-4.00 (m, 2H), 3.28-3.51 (m, 1H), 2.75-2.94 (m, 2H), 2.07 (s, 3H). 13CNMR (125 MHz, CDCl3) 168.4, 155.85, 139.41, 139.36, 138.22, 135.43, 129.15, 128.68, 128.56, 128.37, 128.10, 127.72, 127.41, 127.64, 126.75, 125.62, 123.75, 80.23, 60.18, 54.14, 50.15, 47.99, 37.43, 17.1.

Workup

  1. washit was then washed with water
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70e88e55d312470c8bf3ab4440bb732a
Source dataset
uspto-grants-2012_04
Patent number
US08163953B2

Reaction notes

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