Hydrochloric Acid → HCID 178514085, compound

HRID 380174Notes

Reaction equation

HRID 380174 reaction equation
[CH2:1]([NH:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:13][C:14](=[O:23])[C@H:15]([CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1)[NH2:16].CO.[OH-].[Na+].Cl>C1COCC1.C(OCC)(=O)C.O>[CH2:1]([NH:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C@H:15]([C:14]([OH:23])=[O:13])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 178501499HCID 178501499, compound

Product 1

HCID 178514085HCID 178514085, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the ester from Step 1 (1.9 g, 3.5 mmol) in THF:methanol (10 mL each) and water (2 mL) was added sodium hydroxide (0.4 g, 10 mmol), and the solution was stirred overnight at room temperature. The solution was added to 1N HCl:ethyl acetate (30 mL each). The organic layer was separated and washed with 1N HC1, brine, dried over MgSO4, and concentrated. The product was obtained as a white foam (0.53 g, 53%); ES-MS 289 (m+1).

Workup

  1. customThe organic layer was separated
  2. washwashed with 1N HC1, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-02e8fb2d354c4dedaa1fc040d424a102
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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