N-Methylaniline → Fmoc-3-nitro-O-(dibenzylphosphoryl)tyrosine

HRID 64520Notes

Reaction equation

HRID 64520 reaction equation
C([O:4][C:5](=[O:52])[C@H:6]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][P:33]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])=[C:28]([N+:49]([O-:51])=[O:50])[CH:27]=1)[NH:7][C:8]([O:10][CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])C=C.CNC1C=CC=CC=1.CCOC(C)=O.OS([O-])(=O)=O.[K+]>C1COCC1>[C:8]([NH:7][C@H:6]([C:5]([OH:52])=[O:4])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][P:33]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:34])=[C:28]([N+:49]([O-:51])=[O:50])[CH:27]=1)([O:10][CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9]

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 86720298Fmoc-3-nitro-O-(dibenzylphosphoryl) tyrosine allyl ester

Product 1

HCID 86720297Fmoc-3-nitro-O-(dibenzylphosphoryl)tyrosineYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesis Fmoc-3-nitro-O-(dibenzylphosphoryl)tyrosine allyl ester 3 (3.15 g, 4.2 mmol) was dissolved in dry THF (20 mL), after which N-methylaniline (1.40 mL, 12.9 mmol) and tetrakis triphenylphosphine palladium (254 mg, 0.22 mmol) were added. After stirring for 2 h at room temperature under a N2-atmosphere in the dark, EtOAc (50 mL) and 1M KHSO4 (50 mL) were added. After drying on Na2SO4 and column chromatography (5% MeOH in DCM), the product (2.72 g, 91%) was obtained as a light yellow foam.

Workup

  1. additionwere added
  2. dry with materialAfter drying on Na2SO4 and column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-8cd9a04454d240238394b8df924138ac
Source dataset
uspto-grants-2016_09
Patent number
US09448237B2

Reaction notes

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