Benzyl chloroformate → HCID 22614951, compound

HRID 843134Notes

Reaction equation

HRID 843134 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([CH2:33][OH:34])=[CH:30][C:29]=2[CH:35]=1.C([O-])([O-])=O.[K+].[K+].[CH2:42](OC(Cl)=O)[C:43]1C=CC=CC=1>C1COCC1.O>[CH2:42]([O:34][CH2:33][C:31]1[O:32][C:28]2[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]5[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=5)[C:6]=4[C:2]=3[CH3:1])=[CH:35][C:29]=2[CH:30]=1)[CH3:43]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 22614988HCID 22614988, compound

Product 1

HCID 22614951HCID 22614951, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of the compound in Example 40 (15 mg, 0.03 mmol) in anhydrous THF/H2O were added K2CO3 and benzyloxycarbonyl chloride (3 eq), the mixture was stirred for 3 hours. The crude mixture was purified over SiO2 column. The product was dissolved in anhydrous DMF (2 ml), NaH (5 mg) was added. The mixture was stirred for 10 minutes. Ethyl bromide (excess) was added to the reaction flask. The mixture was stirred for one hour. The crude product was hydrogenated over 10% Pd/C in MeOH to give the desired product as a colorless oil. ESI-MS: m/z 501 (MH+); 1H-NMR (CDCl3): δ 1.36 (3H, t, J=6.9 Hz), 2.16 (2H, m), 2.43 (3H, s), 2.98 (2H, t, J=6.9 Hz), 3.72 (2H, q, J=6.9 Hz), 3.94 (2H, s), 4.25 (2H, t, J=5.9 Hz), 4.68 (2H, s), 5.20 (2H, s), 5.40 (2H, s), 6.69 (1H, d, J=7.9 Hz), 6.73 (1H, s), 7.08 (1H, dd, J=9 Hz, 2.5 Hz), 7.18 (1H, d, J=18 Hz), 7.25-7.32 (3H, m), 7.46 (1H, d, J=9 Hz), 7.75 (1H, d, J=7.9 Hz), 8.59 (1H, dd, J=5 Hz, 1.5 Hz), 8.66 (1H, d, J=1.5 Hz).

Workup

  1. customThe crude mixture was purified over SiO2 column
  2. dissolutionThe product was dissolved in anhydrous DMF (2 ml)
  3. additionNaH (5 mg) was added
  4. stirringThe mixture was stirred for 10 minutes
  5. additionEthyl bromide (excess) was added to the reaction flask
  6. stirringThe mixture was stirred for one hour

Sources & evidence

ORD record
ord-eecf5705e1fb4d6bb58c9a756dc1bc63
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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