Hydrochloric Acid → HCID 11521987, compound

HRID 863189Notes

Reaction equation

HRID 863189 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:15]([OH:17])=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:54][NH:55][O:56][CH3:57].Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:15]([N:55]([CH3:54])[O:56][CH3:57])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14232N,O-DimethylhydroxylamineHCID 81531Diisopropylethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2817957(2S)-2-((ethoxycarbonyl)amino)-3-phenylpropanoic acid

Product 1

HCID 11521987HCID 11521987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 400 μL CH2Cl2 was added 47.4 mg (200 μmole) of EtOCO-Phe, 34.8 mL (200 μmole) DIEA, and 88.4 mg (200 μmole) BOP. After 3 min, 19.4 mg (200 μmole) N,O-dimethyl-hydroxylamine.HCl and 34.8 mL (200 μmole) DIEA were added. The reaction was monitored by TLC, and after 45 min it was diluted with CH2Cl2, washed 2× with dilute HCl and 2× with saturated NaHCO3. The organic layer was dried with Na2SO4, filtered, and the filtrate evaporated by rotary evaporation to give the title compound. NMR (300 MHz, CDCl3): δ 7.20 (m, Ph, 5H), 4.82 (br m, Phe-α, 1H), 4.00 (q, CH3 CH2OCO, 2H), 3.62 (s, N(CH3)OCH3, 3H), 3.11 (s, N(CH3)OCH3, 3H), 3.00 (dd, Phe-b, 1H), 2.85 (dd, Phe-b, 1H), 1.17 (t, CH3CH2OCO, 3H).

Workup

  1. washwashed 2× with dilute HCl and 2× with saturated NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. customthe filtrate evaporated by rotary evaporation

Sources & evidence

ORD record
ord-cfdf087277f8492d92ff181dd3a28d03
Source dataset
uspto-grants-1998_02
Patent number
US05719296

Reaction notes

Loading…