Acetic Acid → HCID 67074171, compound

HRID 2095488Notes

Reaction equation

HRID 2095488 reaction equation
CO[C:3](=[O:20])[C@@H:4]([N:6]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:7][CH:8]=O)[CH3:5].Cl.[C:22]([O:26][C:27](=[O:31])[CH2:28][CH2:29][NH2:30])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][N:30]([CH2:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:31])[C:3](=[O:20])[C@@H:4]1[CH3:5])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester

Product 1

HCID 67074171HCID 67074171, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-2-[benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester (1.25 g, 4.50 mmol) in dichloromethane (25 mL) was added at room temperature dropewise to a suspension of 3-amino-propionic acid tert-butyl ester hydrochloride (0.86 g, 4.70 mmol), triethylamine (0.66 ml, 4.70 mmol), acetic acid (0.51, 9.00 mmol), and sodium triacetoxyborohydride (1.09 g, 5.10 mmol) in dichloromethane (12.5 mL) and stirred over night. The reaction was extracted with aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried over Na2SO4 to yield after evaporation of the solvent 1.21 g (58%) of the titled compound as light yellow oil. MS: 377.3 (MH+)

Workup

  1. extractionThe reaction was extracted with aqueous 10% KHSO4/EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customto yield
  5. customafter evaporation of the solvent 1.21 g (58%) of the titled compound as light yellow oil

Sources & evidence

ORD record
ord-7f89c700b564447fb914610c0c245f3c
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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