(S)-2-amino-4-phenylbutanoic acid → HCID 54520663, compound

HRID 1597662Notes

Reaction equation

HRID 1597662 reaction equation
C1COCC1.O.[NH2:7][C@@H:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([OH:11])=[O:10].[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[O:25][C:24]=2[CH:23]=[CH:22][C:21]=1[S:33](Cl)(=[O:35])=[O:34]>C(N(CC)CC)C>[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[O:25][C:24]=2[CH:23]=[CH:22][C:21]=1[S:33]([NH:7][C@@H:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([OH:11])=[O:10])(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 2724505(S)-2-amino-4-phenylbutanoic acidHCID 27580308-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chlorideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 54520663HCID 54520663, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a THF/water (5:3, 8 mL) solution of (S)α-amino4-phenyl-butyric acid (0.61 g, 0.0034 mol) and triethylamine (1 mL) at 10° C. was added dibenzofuran-2-sulfonyl chloride (1.0 g, 0.00375 mol) in one portion with stirring. The resulting solution was stirred at room temperature for 24 hours. The solution was then concentrated in vacuo and the residue redissolved in water (10 mL). This solution was cooled in an ice bath and then acidified with 1N HCl. An oil was deposited, which was then triturated with ethyl acetate and hexane to give the title product (0.54 g, 35%), Melting point=130-132° C.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 24 hours
  2. concentrationThe solution was then concentrated in vacuo
  3. dissolutionthe residue redissolved in water (10 mL)
  4. temperatureThis solution was cooled in an ice bath
  5. customwhich was then triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-587c33a2efc74dccb9ead93ded78f5ce
Source dataset
uspto-grants-2001_09
Patent number
US06294674B1

Reaction notes

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