N-(tert-butoxycarbonyl)glycine → HCID 20258244, compound

HRID 1583742Notes

Reaction equation

HRID 1583742 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:13][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[N:9]=1.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:13][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[N:9]=1)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 8383952-(2-Amino-phenyl)-benzo[d][1,3]oxazin-4-one

Product 1

HCID 20258244HCID 20258244, compound

Procedure

Using identical reaction conditions as described for the synthesis of the compounds of formula VII of Scheme 2 above, 480 mg (2.0 mmole) of 2-(2-aminophenyl)-3,1-benzoxazin-4-one was reacted with 525 mg (3.0 mmole) of tert-butyloxycarbonylglycine to give 170 mg of the chromatographically-homogeneous tilted compound in 60% overall yield after three cycles.

Workup

  1. customreaction conditions
  2. customto give 170 mg of the
  3. customoverall yield after three cycles

Sources & evidence

ORD record
ord-246ab69e470f453ba6ac0a497e68561e
Source dataset
uspto-grants-1985_11
Patent number
US04554272

Reaction notes

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