Glycine → HCID 66861293, compound

HRID 1465933Notes

Reaction equation

HRID 1465933 reaction equation
C(O[C:6]([C:8]1[N:13]=[CH:12][C:11]2[CH:14]=[C:15]([S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:16][C:10]=2[C:9]=1[OH:24])=[O:7])CCC.[NH2:25][CH2:26][C:27]([OH:29])=[O:28]>C[O-].[Na+].CO.Cl>[OH:24][C:9]1[C:10]2[S:16][C:15]([S:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][C:11]=2[CH:12]=[N:13][C:8]=1[C:6]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:7]

Participants

6

Reactant 2

HCID 750GlycineHCID 67233165HCID 67233165, compound

Product 1

HCID 66861293HCID 66861293, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
120 °C

Procedure

7-Hydroxy-2-phenylsulfanyl-thieno[3,2-c]pyridine-6-carboxylic acid n-butyl ester, example 17.c.A, (25 mg, 0.07 mmol) and glycine (52 mg, 0.7 mmol) were suspended in 1.4 mL of 0.5 N NaOMe in methanol. The reaction mixture was heated at 120° C. for 10 minutes using a CEM microwave reactor, cooled, and diluted with 0.25 N HCl to precipitate out a white solid. The precipitate was collected on a fine glass fritted filter, washed twice with water, and dried under hi-vacuum to isolate 23 mg of the title compound. MS: (+) m/z 361.4 (M+1).

Workup

  1. temperaturecooled
  2. customto precipitate out a white solid
  3. customThe precipitate was collected on a fine glass fritted filter
  4. washwashed twice with water
  5. customdried under hi-vacuum

Sources & evidence

ORD record
ord-3a25f1fd21bc4959912167d1cf812678
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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