HCID 68292566, compound → (3S)-3-[[8,8-dioxo-9-(4-phenylphenyl)-2,5-dioxa-8lambda6-thia-7-azaspiro[3.5]non-6-en-6-yl]amino]-3-(2-fluorophenyl)propan-1-ol

HRID 339897Notes

Reaction equation

HRID 339897 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@H:11]([NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])(C(C)(C)C)(C)C.[C:20]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=[CH:24][C:23]([CH:26]2[C:31]3([CH2:34][O:33][CH2:32]3)[O:30][C:29](OC)=[N:28][S:27]2(=[O:38])=[O:37])=[CH:22][CH:21]=1>ClCCl>[C:20]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=[CH:24][C:23]([CH:26]2[C:31]3([CH2:32][O:33][CH2:34]3)[O:30][C:29]([NH:19][C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[CH2:10][CH2:9][OH:8])=[N:28][S:27]2(=[O:37])=[O:38])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68292566HCID 68292566, compoundHCID 68292582(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine

Product 1

HCID 178527197(3S)-3-[[8,8-dioxo-9-(4-phenylphenyl)-2,5-dioxa-8lambda6-thia-7-azaspiro[3.5]non-6-en-6-yl]amino]-3-(2-fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round-bottom flask, 9-biphenyl-4-yl-6-methoxy-2,5-dioxa-8-thia-7-azaspiro[3.5]non-6-ene 8,8-dioxide was dissolved under inert gas in 2 ml of dichloromethane, and 151 mg of (S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine were added. After concentration by rotary evaporation, the residue was left to stand at room temperature for 18 hours. To detach the protecting group, the residue was taken up in 1 ml of methanol and, after addition of 0.05 ml of concentrated hydrochloric acid, stirred at room temperature for 1 hour. After concentration by rotary evaporation, the residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and freed of the solvent under reduced pressure. This gave the product (8 mg) with a molecular weight of 496.6 g/mol (C26H25FN2O5S); MS (ESI): m/e=497 (M+H+).

Workup

  1. concentrationAfter concentration
  2. customby rotary evaporation
  3. waitthe residue was left
  4. additionafter addition of 0.05 ml of concentrated hydrochloric acid
  5. concentrationAfter concentration
  6. customby rotary evaporation
  7. customthe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-b6c0f7003572428c89a3232014035e5e
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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