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4-Nitrophenyl formate → tert-Butyl {2-(formylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 220635
Notes
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Reaction equation

HRID 220635 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.[CH:22](OC1C=CC([N+]([O-])=O)=CC=1)=[O:23]>C1COCC1>[CH:22]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 746284-Nitrophenyl formateHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536815tert-Butyl {2-(formylamino)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Of the compound from Example 22A, 75 mg (0.25 mmol) were introduced in 1.5 ml of THF and admixed at 0° C. in small portions with 43.25 mg (0.26 mmol) of 4-nitrophenyl formate. The mixture was stirred at 0° C. for 2 h and then at RT overnight. The solvent was removed on a rotary evaporator and the residue was taken up in DMSO and purified by preparative HPLC (method 10). This gave 66 mg (81% of theory) of the title compound.

Workup

  1. customat RT
  2. customovernight
  3. customThe solvent was removed on a rotary evaporator
  4. custompurified by preparative HPLC (method 10)

Sources & evidence

ORD record
ord-7a916c4c03b0407bb00d937789e968a8
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202895B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes