Glycine → HCID 123709625, compound

HRID 1509372Notes

Reaction equation

HRID 1509372 reaction equation
[NH2:1][CH2:2][C:3](O)=O.[OH-].[Na+].Cl[CH2:9][C:10]1[CH:18]=[CH:17]C=C[C:11]=1[C:12](Cl)=O.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].[N:31]([C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1C=O)=[N+:32]=[N-:33]>O.C(#N)C.C(N(CC)CC)C>[N:31]([C:34]1[CH:35]=[CH:38][C:39]([CH:3]=[C:2]2[C:26](=[O:27])[O:28][C:29]([C:30]3[CH:17]=[CH:18][C:10]([CH2:9][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:11][CH:12]=3)=[N:1]2)=[CH:40][CH:41]=1)=[N+:32]=[N-:33]

Participants

10

Reactant 6

HCID 750Glycine4×HCID 8083MorpholineHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide2×HCID 30163952-(Chloromethyl)benzoyl chlorideHCID 108880602-azidobenzaldehyde

Product 1

HCID 123709625HCID 123709625, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

Glycine (3 g) was dissolved in a mixture of water (20 g), acetonitrile (10 g), and sodium hydroxide (2 g), and the solution was cooled to 10° C., to thereby prepare a glycine solution. Separately, chloromethylbenzoyl chloride (8 g) was dissolved in acetonitrile (20 g), and the solution was cooled to 10° C. The liquid was added dropwise to the glycine solution over 2 hours. Simultaneously, a solution of sodium hydroxide (2 g) dissolved in water (20 g) was added to the glycine solution over 2 hours. Five hours later, morpholine (4 g) was added thereto, and the mixture was allowed to react at 60° C. for 4 hours, followed by cooling the resultant solution to 10° C. Triethylamine (4 g) was further added, and then ethyl chloroformate (4.5 g) was added dropwise thereto over 30 minutes. The resultant mixture was continuously stirred for 2 hours. Subsequently, azidobenzaldehyde (3.5 g) was added, and the mixture was allowed to react at 20° C. for 16 hours. The thus-formed precipitates were separated through filtration and dried, to thereby yield 1 g of photosensitive material G as a target compound. Photosensitive material G was dissolved in acetonitrile, and a UV absorption spectrum of the solution was measured, and an absorption peak attributed to an azlactone ring was identified at 387 nm. FIG. 3 illustrates the UV absorption spectrum of photosensitive material G.

Workup

  1. temperaturethe solution was cooled to 10° C
  2. customto react at 60° C. for 4 hours
  3. customto react at 20° C. for 16 hours
  4. customThe thus-formed precipitates
  5. customwere separated through filtration
  6. customdried
  7. dissolutionPhotosensitive material G was dissolved in acetonitrile
  8. customa UV absorption spectrum of the solution
  9. customthe UV absorption spectrum of photosensitive material G

Sources & evidence

ORD record
ord-9c0c837c32414ee49a6072ccf8887e28
Source dataset
uspto-grants-2015_12
Patent number
US09223210B2

Reaction notes

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