Hydrochloric Acid → HCID 513971, compound

HRID 987973Notes

Reaction equation

HRID 987973 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:20](=[O:44])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]([N:29]([S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27][OH:28])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.Cl>C(O)C>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[C:20]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]([N:29]([S:34]([C:37]1[CH:38]=[CH:39][C:40]([NH2:43])=[CH:41][CH:42]=1)(=[O:36])=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27][OH:28])=[O:44]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59100715HCID 59100715, compound

Product 1

HCID 513971HCID 513971, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester (698 mg, 1.089 mmol) was added to 6 mL of ethanol and 6 mL of HCl. The mixture was stirred at room temperature until completion by TLC. The ethanol was evaporated and the acidic mixture was poured into an extracting funnel containing 75 mL of ethyl acetate and 50 mL of HCl 1M and separated. The aqueous layer was washed with ethyl acetate. The aqueous phase was basified with pellets of NaOH and poured into an extracting funnel. The organic layer was washed with NaOH 1M and brine, dried over sodium sulfate, filtered, evaporated and dried under vacuum to give 544 mg (92%) of a yellow solid (Rf=0, 100% EtOAc, indicator: ninhydrin).

Workup

  1. customThe ethanol was evaporated
  2. additionthe acidic mixture was poured into an extracting funnel
  3. additioncontaining 75 mL of ethyl acetate and 50 mL of HCl 1M
  4. customseparated
  5. washThe aqueous layer was washed with ethyl acetate
  6. additionpoured into an extracting funnel
  7. washThe organic layer was washed with NaOH 1M and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-6dc7a7e18a4d44c69efd60d62a41adad
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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