Benzyl succinimido carbonate → HCID 22877443, compound

HRID 1740255Notes

Reaction equation

HRID 1740255 reaction equation
[NH2:1][C:2]([CH3:20])([CH3:19])[C:3]([NH:5][C@@H:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:9]=2[NH:8][C:7]1=[O:18])=[O:4].[CH2:21]([O:28][C:29](ON1C(=O)CCC1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH2:21]([O:28][C:29]([NH:1][C:2]([CH3:20])([CH3:19])[C:3]([NH:5][C@@H:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:9]=2[NH:8][C:7]1=[O:18])=[O:4])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 22877423HCID 22877423, compound

Product 1

HCID 22877443HCID 22877443, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 33 mg (0.12 mmol) of 2-amino-2-methyl-N-[7-fluoro-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide (Step D) in 1 mL of methylene chloride was 32 mg (0.13 mmol) of N-(benzyloxycarbonyloxy)succinimide. The soution was stirred at room temperature for 24 hours then quenched with 5 drops of 33% aqueous ammonium hydroxide. The solvent was removed under vacuum and the residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes (75:25) to afford 25 mg (46%) of the product as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 1.48 (s, 3H), 1.50 (s, 3H), 1.82 (m, 1H), 2.56 (m, 1H), 2.71 (m, 1H), 2.86 (m, 1H), 4.42 (m, 1H), 5.05 (s, 2H), 5.43 (s, 1H), 6.90 (m, 2H), 7.09 (d, 8 Hz, 1H), 7.30 (m, 5H), 8.09 (s, 1H). FAB-MS: calculated for C22H24FN3O4 413; found 414 (M+H, 100%).

Workup

  1. customthen quenched with 5 drops of 33% aqueous ammonium hydroxide
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes (75:25)

Sources & evidence

ORD record
ord-f7c927046c964e0b9739b77adf25b844
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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