Acetonitrile → HCID 86590989, compound

HRID 982663Notes

Reaction equation

HRID 982663 reaction equation
[C:1]([C@H:4]([N:6]1[C:11](=[O:12])[C@@H:10]([NH2:13])[C@@H:9]([OH:14])[CH2:8][O:7]1)[CH3:5])([OH:3])=[O:2].C([O-])(O)=O.[Na+].[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC#N>O>[C:1]([C@H:4]([N:6]1[C:11](=[O:12])[C@@H:10]([NH:13][C:27](=[O:28])[CH2:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:9]([OH:14])[CH2:8][O:7]1)[CH3:5])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 86590988HCID 86590988, compound

Product 1

HCID 86590989HCID 86590989, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the amino acid 13 (0.290 g, 1.36 mmol) and NaHCO3 (0.343 g, 4.08 mmol) in water (7 mL), a solution of phenylacetyl chloride (0.191 g, 1.24 mmol) in abs. MeCN (3 mL) was added dropwise with cooling (−5˜−6° C.) and stirring. The reaction mixture was stirred for 2 h at 0˜−2° C. and for 1 hour at room temperature and was concentrated in vacuo to a volume of circa 5 mL. The solution was cooled to ca. 5° C. and adjusted to pH 2-3 with 1M aqueous HCl. (2.8 mL). The white precipitate was filtered off, washed with water and dried in vacuo to afford 0.364 g (91%) of the product 14 as a white solid with mp 194-195° C. (decomp.) (from iso-PrOH). 1H NMR (400 MHz) in CD3OD (J, Hz): δ 1.47 (3H, d, 3J=7.3, α-MeCH), 3.62 (1H, d, 2J=−14.8, CHAPh), 3.67 (1H, d, 2J=−14.8, CHBPh), 4.06 (1H, dd, 2J=−11.4, 3J=3.7, 6-HA), 4.12-4.06 (1H, m, 5-H), 4.33 (1H, dd, 2J=−11.4, 3J=5.6, 6-HB), 4.66 (1H, d, 3J=8.0, 4-H), 4.96 (1H, q, 3J=7.3, α-CH), 7.38-7.17 (5H, m, Ph). 13C (100 MHz) in CD3OD: δ 1371, 43.63, 55.70, 57.54, 71.84, 79.10, 127.85, 129.51, 130.37, 136.63, 169.61, 172.71, 174.89. IR (KBr), cm−1: 3361, 2913, 1729, 1666, 1630, 1542, 1440, 1233. MS (CI, isobutane), m/Z: 323 (M++1). Anal. Calcd for C15H18N2O6: C, 55.9; H, 5.6; N, 8.7. Found: C, 55.7; H, 5.7; N, 8.6%.

Workup

  1. temperaturewith cooling (−5˜−6° C.)
  2. stirringThe reaction mixture was stirred for 2 h at 0˜−2° C. and for 1 hour at room temperature
  3. concentrationwas concentrated in vacuo to a volume of circa 5 mL
  4. filtrationThe white precipitate was filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-062e775650384e3bb6510c3843b8d528
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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