Water → HCID 44464416, compound

HRID 1698444Notes

Reaction equation

HRID 1698444 reaction equation
[C:1]([NH:11][C@@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:13]([OH:23])[CH:14]([NH2:22])CC1C=CC=CC=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:31]=[C:32]1[O:36][C:34](=[O:35])[CH2:33]1.O>C(O)C.ClCCl>[C:1]([NH:11][C@@H:12]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C@H:13]([OH:23])[CH2:14][N:22]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:34](=[O:35])[CH2:33][C:32](=[O:36])[CH3:31])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 12661DiketeneHCID 86635874HCID 86635874, compound

Product 1

HCID 44464416HCID 44464416, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The Cbz protected amino alcohol (IX) (0.080 g, 0.19 mmol) was dissolved in 2 ml of ethanol and to this diketene (23 μL, 0.29 mmol) was added dropwise. The reaction mixture was then stirred for 1 hour and diluted with 4 ml dichloromethane. It was then poured into water and the organic layer was separated, and dried (Na2SO4). It was then subjected to silica gel chromatography with 2:1 hexane/ethyl acetate as an eluent to give the keto-amide (XI) as oil. 100 mg (98% yield) 1H NMR (500 MHz, CDCl3) δ 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), 2.43 (s, 2H), 2.05 (s, 3H). 13CNMR (125 MHz, CDCl3) 201.2, 168.4, 155.85, 140.91, 140.36, 138.22, 129.15, 128.68, 128.56, 128.37, 128.10, 127.72, 127.41, 127.64, 126.75, 80.23, 60.18, 54.14, 50.15, 7.99, 43.6, 37.43, 25.7.

Workup

  1. additionwas added dropwise
  2. customthe organic layer was separated
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-f978c7a00b3d4102ad8347a4c7f27f0d
Source dataset
uspto-grants-2012_04
Patent number
US08163953B2

Reaction notes

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