Pyridine → HCID 86621600, compound

HRID 2190222Notes

Reaction equation

HRID 2190222 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:25]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:24]=1)[C:14]([O:16][C@H:17]([CH3:21])[C@H:18]([OH:20])[CH3:19])=[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]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:25]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:24]=1)[C:14]([O:16][C@H:17]([CH3:21])[C@H:18]([O:20][C:1](=[O:3])[CH3:2])[CH3:19])=[O:15])=[O:11])([CH3:7])([CH3:8])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 60207249HCID 60207249, compound

Product 1

HCID 86621600HCID 86621600, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (0.39 mL, 5.5 mmol) and (1R,2R)-2-hydroxy-1-methylpropyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (32) (2.0 g, 3.6 mmol) were dissolved in 25 mL of anhydrous dichloromethane. A solution of pyridine (0.5 mL, 5.5 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 and drying under vacuum, the crude product (33) (2.0 g, 95% yield) was isolated and used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3): δ 1.11 (d, J=6.4 Hz, 3H), 1.15 (d, J=6.4 Hz, 3H), 1.43 (s, 9H), 2.05 (s, 3H), 2.95 (dd, J=13.6, 6.4 Hz, 1H), 3.00 (dd, J=13.6, 6.4 Hz, 1H), 4.50 (dd, J=13.6, 6.4 Hz, 1H), 4.93 (m, 2H), 4.98 (d, 1H, NH), 5.12 (s, 4H), 6.66 (dd, J=8.0, 2.0 Hz, 1H), 6.77 (d, J=2.0 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 7.29-7.45 (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
  5. customdrying under vacuum

Sources & evidence

ORD record
ord-11c9b0fd7b2e40b9bb1d99e03e1fb60e
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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