Hydrochloric Acid → HCID 9914513, compound

HRID 636704Notes

Reaction equation

HRID 636704 reaction equation
C[O:2][C:3](=[O:39])[C@H:4]([CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:28]2[N:29]=[C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:31][CH:32]=2)=[CH:21][CH:20]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[OH-].[Li+].Cl.C(#N)C>O1CCCC1.O>[CH2:9]([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:39])=[O:2])[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:28]2[N:29]=[C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:31][CH:32]=2)=[CH:21][CH:20]=1)=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 15487825HCID 15487825, compound

Product 1

HCID 9914513HCID 9914513, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2 °C

Procedure

To a solution of crude N-benzyloxycarbonyl-O-(4-(2-(2-phenyloxazol-4-yl)ethoxy)phenyl)methyl-L-serine methyl ester (13.32 g, 25.1 mmol) in 133 mL of tetrahydrofuran at 2° C. was added 44 mL of deionized water. A solution of lithium hydroxide (1.2 g, 50.2 mmol) in 40 mL of deionized water was added slowly over 25 minutes keeping the temperature of the reaction below 4° C. After the addition was complete the reaction was allowed to stir at 2° C. for 1 hour. The pH of the mixture was adjusted to about 1 with 6 N hydrochloric acid (8.3 mL). Water (130 mL) was added and the reaction was extracted with ethyl acetate (2×260 mL). The organic extracts were dried over magnesium sulfate, filtered, and the solvent removed to give an oil that was solvent exchanged into 125 mL of acetonitrile. The product crystallized and the slurry was stirred for about 1 hour at about 2° C. The precipitate was filtered using filtrete and rinsed with cold acetonitrile to give 7.65 g of the title compound.

Workup

  1. customthe temperature of the reaction below 4° C
  2. additionAfter the addition
  3. extractionthe reaction was extracted with ethyl acetate (2×260 mL)
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give an oil that
  8. customThe product crystallized
  9. stirringthe slurry was stirred for about 1 hour at about 2° C
  10. filtrationThe precipitate was filtered
  11. washrinsed with cold acetonitrile

Sources & evidence

ORD record
ord-7d291ca6f3d249d0b21a8ece1112c971
Source dataset
uspto-grants-2001_02
Patent number
US06194446B1

Reaction notes

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