Hydrochloric Acid → HCID 67915300, compound

HRID 2372602Notes

Reaction equation

HRID 2372602 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]([CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:5])[CH3:3].O=[C:22]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24].C([BH3-])#N.[Na+].[ClH:40]>O.C(O)C>[ClH:40].[CH2:26]([O:25][C:23]([CH:22]([NH:1][C@H:2]([C:4]([N:6]([CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:5])[CH3:3])[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 13132291HCID 13132291, compound

Product 1

HCID 67915300HCID 67915300, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

L-Alanyl-N-(indan-2-yl)-β-alanine (2.0 g) is dissolved in a mixture of 20 ml of water and 100 ml of ethanol, 10 g of ethyl 2-oxo-4-phenylbutyrate is added, and a solution of 0.94 of sodium cyanoborohydride in 20 ml of ethanol is added dropwise over 2 hours. The mixture is stirred at room temperature for 3 hours and then adjusted to pH 4.0 with 10% hydrochloric acid, and the ethanol is distilled off under reduced pressure. The residue is extracted with 200 ml of ethyl acetate, washed with water and dried, and the ethyl acetate is distilled off under reduced pressure. The residue is dissolved in 2 ml of 20% ethanolic hydrochloric acid, 100 ml of ethyl ether is added, and the mixture is allowed to stand at room temperature. Thus is obtained 1.2 g of N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-N-(indan-2-yl)-β-alanine hydrochloride as colorless amorphous powder. NMR Spectrum (d6 -DMSO) δ: 1.30(3H,t,J=7.5Hz), 1.40(3H, d,J=4.5Hz), 2.65-3.00(4H,m,CH2), 3.20-3.40(4H,m,CH2), 4.25(2H,q,J=7.5Hz,CH2), 7.20(4H,s,Ph), 7.30(5H,s,Ph)

Workup

  1. additionis added
  2. distillationthe ethanol is distilled off under reduced pressure
  3. extractionThe residue is extracted with 200 ml of ethyl acetate
  4. washwashed with water
  5. customdried
  6. distillationthe ethyl acetate is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in 2 ml of 20% ethanolic hydrochloric acid
  8. addition100 ml of ethyl ether is added
  9. customto stand at room temperature

Sources & evidence

ORD record
ord-cd92e2b198674016a98aefd6f7d8c242
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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