Pyridine → HCID 66949207, compound

HRID 2190217Notes

Reaction equation

HRID 2190217 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:24]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:23]=1)[C:14]([O:16][C@H:17]([CH3:20])[CH2:18][OH:19])=[O:15])=[O:11])([CH3:8])([CH3:7])[CH3:6].N1C=CC=CC=1>ClCCl>[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[C:24]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:23]=1)[C:14]([O:16][C@H:17]([CH3:20])[CH2:18][O:19][C:1](=[O:3])[CH3:2])=[O:15])=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66952297HCID 66952297, compound

Product 1

HCID 66949207HCID 66949207, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (2.3 mL, 33.1 mmol) and (1R)-2-hydroxy-1-methylethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (17) (11.8 g, 22.1 mmol) were dissolved in 400 mL of anhydrous dichloromethane. A solution of pyridine (2.7 mL, 33.1 mmol) in dichloromethane was added dropwise at 0° C. The mixture was stirred at room temperature for 2 hours. The product was extracted with dichloromethane, washed with 5% NaHCO3, 10% citric acid, and dried over Na2SO4. After concentration the resulting residue was further dried under vacuum. The crude product (18) (12.9 g, 100% yield) was isolated as a foamy solid. 1H NMR (400 MHz, CDCl3): δ 1.15 (d, J=6.4 Hz, 3H), 1.43 (s, 9H), 2.03 (s, 3H), 2.95 (dd, J=14.0, 6.8 Hz, 1H), 3.01 (dd, J=14.0, 6.8 Hz, 1H), 3.99 (dd, J=12.0, 6.4 Hz, 1H), 4.12 (dd, J=12.0, 3.2 Hz, 1H), 4.50 (dd, J=14.0, 6.8 Hz, 1H), 4.93 (d, 1H, NH), 5.07 (m, 1H), 5.10 (s, 4H), 6.65 (dd, J=8.0, 2 Hz, 1H), 6.76 (d, J=2.0 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 7.28-7.46 (m, 10H).

Workup

  1. extractionThe product was extracted with dichloromethane
  2. washwashed with 5% NaHCO3, 10% citric acid
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration the resulting residue
  5. customwas further dried under vacuum

Sources & evidence

ORD record
ord-a5e5ac68eada459c85af99051645e896
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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