Methanol → HCID 86756616, compound

HRID 324294Notes

Reaction equation

HRID 324294 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][N:8]([CH2:17][C:18]([OH:20])=[O:19])[C:7]1=[O:21].[CH3:22]O>>[NH2:5][C@H:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][N:8]([CH2:17][C:18]([O:20][CH3:22])=[O:19])[C:7]1=[O:21]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 54121153(4S)-4-Amino-1,3,4,5-tetrahydro-3-oxo-2H-2-benzazepine-2-acetic acid

Product 1

HCID 86756616HCID 86756616, compoundYield 97%

Procedure

MeOH (5 mL) was cooled with an ice-acetone bath, and thionyl chloride (60 μL) was added. This solution was stirred for 1 min, and then the amino acid from Example 7 (163 mg, 0.70 mmol) was added all at once. After removing the cooling bath, the reaction was stirred while warming to ambient temperature over 1 hr, and then heated to 40° C. for another 1.5 hr. When the reaction mixture was concentrated to dryness, HPLC analysis of the residue indicated that the reaction was incomplete, so the above reaction sequence was repeated, this time heating the reaction for 0.5 hr at the end. The reaction mixture was concentrated to dryness, giving the product as a light yellow solid (168 mg, 97%).

Workup

  1. customAfter removing the cooling bath
  2. stirringthe reaction was stirred
  3. temperatureheated to 40° C. for another 1.5 hr
  4. concentrationWhen the reaction mixture was concentrated to dryness, HPLC analysis of the residue
  5. temperaturethis time heating
  6. customthe reaction for 0.5 hr at the end
  7. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-f1ec216ca73741cb89fa6edf7a715501
Source dataset
uspto-grants-2001_04
Patent number
US06218382B1

Reaction notes

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