Pyridine → HCID 86679033, compound

HRID 1773090Notes

Reaction equation

HRID 1773090 reaction equation
C(OC([NH:11][C@@H:12]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][OH:14])=O)C1C=CC=CC=1.[NH2:22][C:23]1[C:24]([OH:34])=[C:25]([S:30]([OH:33])(=[O:32])=[O:31])[CH:26]=[C:27]([Cl:29])[CH:28]=1.Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[NH2:11][C@@H:12]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:13][O:14][C:36]([NH:22][C:23]1[C:24]([OH:34])=[C:25]([S:30]([OH:33])(=[O:32])=[O:31])[CH:26]=[C:27]([Cl:29])[CH:28]=1)=[O:38]

Participants

6

Reactant 4

HCID 1049PyridineHCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 94429TriphosgeneHCID 853481N-carbobenzoxy-L-phenylalanilol

Product 1

HCID 86679033HCID 86679033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

285 mg (1 mmol) of (S)-2-(benzyloxycarbonylamino)-3-phenyl-1-propanol, 223 mg (1 mmol) of 3-amino-5-chloro-2-hydroxybenzenesulfonic acid and 100 mg (0.33 mmol) of triphosgene were suspended in 3 ml of methylene chloride, to which 0.7 ml of pyridine was dropwisely added. Following agitation at room temperature overnight, the solvent was distilled away, and the resultant was purified using purification step A to obtain a crude purified substance of the title compound in protected form. To the obtained crude purified substance, 2 ml of 48% hydrogen bromide-acetic acid solution was added, and the resultant was stirred at room temperature for 2 hours. The solvent was distilled away and water and acetonitrile were added to the obtained residue for deposition. The deposited solid substance was filtrated to obtain the title compound.

Workup

  1. additionwas dropwisely added
  2. customat room temperature
  3. customovernight
  4. distillationthe solvent was distilled away
  5. customthe resultant was purified
  6. custompurification step A
  7. customto obtain a crude
  8. custompurified substance of the title compound in protected form
  9. customTo the obtained crude
  10. custompurified substance, 2 ml of 48% hydrogen bromide-acetic acid solution
  11. additionwas added
  12. distillationThe solvent was distilled away
  13. additionwater and acetonitrile were added to the obtained residue for deposition
  14. filtrationThe deposited solid substance was filtrated

Sources & evidence

ORD record
ord-9f68d99d820942459a949ec13bd23faa
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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