Pyridine → HCID 53379288, compound

HRID 1773089Notes

Reaction equation

HRID 1773089 reaction equation
C(OC([NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])=O)(C)(C)C.[NH2:13][C:14]1[C:15]([OH:25])=[C:16]([S:21]([OH:24])(=[O:23])=[O:22])[CH:17]=[C:18]([Cl:20])[CH:19]=1.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[NH2:8][C@@H:9]([CH3:12])[CH2:10][O:11][C:27]([NH:13][C:14]1[C:15]([OH:25])=[C:16]([S:21]([OH:24])(=[O:23])=[O:22])[CH:17]=[C:18]([Cl:20])[CH:19]=1)=[O:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 94429TriphosgeneHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 53379288HCID 53379288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

75 mg (1 mmol) of (S)-2-(tert-butoxycarbonylamino)-1-propanol (Boc-Ala-ol), 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, and added with 0.7 ml of pyridine. Following agitation at room temperature overnight, the solvent was distilled away, purified using purification step A to obtain a crude purified substance of the title compound in protected form. To the resultant crude purified substance, 2 ml of trifluoroacetic acid was added, and the resultant was stirred at room temperature for 2 hours. Subsequently, the solvent was distilled away, and the resulting residue was added with water and acetonitrile for deposition and the deposited solid was filtrated to obtain the title compound.

Workup

  1. customat room temperature
  2. customovernight
  3. distillationthe solvent was distilled away
  4. custompurified
  5. custompurification step A
  6. customto obtain a crude
  7. custompurified substance of the title compound in protected form
  8. customTo the resultant crude purified substance, 2 ml of trifluoroacetic acid
  9. additionwas added
  10. distillationSubsequently, the solvent was distilled away
  11. additionthe resulting residue was added with water and acetonitrile for deposition
  12. filtrationthe deposited solid was filtrated

Sources & evidence

ORD record
ord-48e80a72770644c8867c1ee194efd4e9
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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