Hydrochloric Acid → HCID 22952780, compound

HRID 276766Notes

Reaction equation

HRID 276766 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][OH:9])=[O:5])[CH3:3].FC1C([O:20][C:21](=O)[C@@H:22]2[CH2:26][C@@H:25]([OH:27])[CH2:24][N:23]2C(OC(C)(C)C)=O)=C(F)C(F)=C(F)C=1F.[ClH:40]>CN(C)C=O.C(O)(C)C>[ClH:40].[OH:27][C@H:25]1[CH2:24][NH:23][C@H:22]([C:21]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][OH:9])=[O:5])[CH3:3])=[O:20])[CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15494333303-41-1HCID 22952776HCID 22952776, compound

Product 1

HCID 22952780HCID 22952780, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

N-alanylserine (1.5 kg, 8.515 M) and Boc-trans-4-hydroxy-L-proline (3.72 kg) (prepared as described in step 2) were heated at 50° C. in dimethylformamide (15 L) for 3 hours. The solution was cooled to 20° C., treated with concentrated hydrochloric acid (7.5 L) and stirred at room temperature for 24 hours. The resulting slurry was diluted with isopropanol (30 L), stirred at room temperature for 30 minutes and then cooled to 0° C. for 1 hour. The solid was collected by filtration and washed with isopropanol (20 L). The solid was dried in vacuo at 40° C. to afford the title compound as a white crystalline solid.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. temperaturecooled to 0° C. for 1 hour
  3. filtrationThe solid was collected by filtration
  4. washwashed with isopropanol (20 L)
  5. customThe solid was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-4bed6c16b2094627b46bf18db4007365
Source dataset
uspto-grants-2002_03
Patent number
US06355611B1

Reaction notes

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