Benzyl chloroformate → HCID 178500686, compound

HRID 1713881Notes

Reaction equation

HRID 1713881 reaction equation
N(C(=O)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:5])N.ClC([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O>N1C=CC=CC=1>[CH2:29]([O:28][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1)=[O:5])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 178500682HCID 178500682, compound

Product 1

HCID 178500686HCID 178500686, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Intermediate 43 (3.31 g, 13.40 mmol) in dry pyridine (18 mL) under an inert atmosphere at 0° C. was added benzyl chloroformate (2.30 mL, 16.08 mmol) then allowed to warm to ambient temperature and stirred for 18 hours. After concentrating in vacuo the residue was partitioned between Et2O (150 mL) and 1M aqueous HCl (20 mL). The organic phase was dried (MgSO4), filtered and evaporated to a yellow solid. Purification by chromatography through silica gave the title compound (3.50 g, 68%) as an off white solid; 1H NMR (CDCl3) δ1.03-1.12 (2H, m), 1.35-1.46 (2H, m), 1.74-1.82 (5H, m), 2.17-2.18 (2H, m), 2.33-2.39 (1H, m), 3.61 (3H, s), 5.12 (2H, s), 6.50 (1H, s), 7.06 (2H, d), 7.19-7.34 (7H, m)

Workup

  1. concentrationAfter concentrating in vacuo the residue
  2. customwas partitioned between Et2O (150 mL) and 1M aqueous HCl (20 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a yellow solid
  6. customPurification by chromatography through silica

Sources & evidence

ORD record
ord-7a61513cde464cac9a6863654b9edf1e
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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