Hydrochloric Acid → HCID 86595546, compound

HRID 1477379Notes

Reaction equation

HRID 1477379 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:10]([OH:12])=O.Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:10]([NH:18][CH2:17][C:16]([O:15][CH3:14])=[O:19])=[O:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 69221Glycine methyl esterHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6928266(R)-Indoline-2-carboxylic acid

Product 1

HCID 86595546HCID 86595546, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (2R)-indoline-2-carboxylic acid (1 g, 5.64 mmol) and HCl salt of amino-acetic acid methyl ester (710 mg, 5.64 mmol) and BOP (2.75 g, 1.1 eq) in 15 mL DMF was added 2.95 mL hunig base. The mixture was stirred overnight. The mixture was diluted in sat. NaHCO3, extracted with EtOAc three time, and washed with sat. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated to give the desired methyl {[(2R)-2,3-dihydro-1H-indol-2-ylcarbonyl]amino}acetate. The material was used directly in the next step without further purification.

Workup

  1. extractionextracted with EtOAc three time
  2. washwashed with sat. NaHCO3 and brine
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e5eb3e457be94e749bd23cb4624b6c05
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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