Sodium Carbonate → HCID 13018385, compound

HRID 1352189Notes

Reaction equation

HRID 1352189 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([OH:8])[C:5]([OH:7])=[O:6].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(=O)([O-])[O-].[Na+].[Na+].O[N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH2:13]([O:12][C:10]([NH:1][CH2:2][CH2:3][C@H:4]([OH:8])[C:5]([O:7][N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33])=[O:6])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 27339294-Amino-2-hydroxybutyric acid, (S)-(-)-

Product 1

HCID 13018385HCID 13018385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the N-Cbz protected (S)-4-amino-2-hydroxybutanoic acid (76 mg, 0.300 mmol, prepared from treatment of 1.0 eq. of the acid with 1.2 eq. of benzyl chloroformate in the presence of 2.1 equiv. of sodium carbonate at 0–5° C. overnight, [α]D25=−61°), N-hydroxysuccinimide (38 mg, 0.318 mmol), and DCC (63 mg, 0.300 mmol) in anhydrous THF (3.5 mL) was stirred at room temperature under an atmosphere of argon for 2 h. This solution was directly used for the syntheses of 29–31.

Sources & evidence

ORD record
ord-26ded2bdee154efeb6b671bac5376ae8
Source dataset
uspto-grants-2007_05
Patent number
US07220727B2

Reaction notes

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