Toluene → HCID 66676719, compound

HRID 1766974Notes

Reaction equation

HRID 1766974 reaction equation
[C:1]([NH:18][NH:19][CH3:20])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].N[C@H:28]([C:40]([OH:42])=[O:41])CC1C=C2C(C=CC=C2)=CC=1.[C:43]1([CH3:49])[CH:48]=CC=C[CH:44]=1>>[C:43]([O:42][C:40](=[O:41])[CH2:28][N:18]([C:1]([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[NH:19][CH3:20])([CH3:49])([CH3:48])[CH3:44]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 10796Cesium carbonateHCID 1859152-NaphthylalanineHCID 10516035HCID 10516035, compound

Product 1

HCID 66676719HCID 66676719, compoundYield 70%

Procedure

1 L, two-necked, round-bottom-flask was fitted with a glass stopper and reflux condenser connected to a calcium tube. A solution of N-Fmoc-N′-methyl hydrazine (20 g, 75 mmol) in toluene (300 mL) was added. A solution of t-butylbromo acetate (22 g, 111 mmol) in toluene (50 mL) was added slowly. Cs2CO3 (49 g, 149 mmol) was added slowly. Nal (11 g, 74 mmol) was added slowly with vigorous stirring. The reaction mixture was stirred at reflux temperature over 1 day. The product mixture was filtered and extracted with EA (500 mL). The solution was dried over sodium sulfate and evaporated in vacuo. The product was purified by chromatography with hexane:EA=2:1 solution to give (N-Fmoc-N′-methyl-hydrazino)-acetic acid t-butyl ester (19.8 g, 70%).

Workup

  1. custom1 L, two-necked, round-bottom-flask was fitted with a glass stopper
  2. temperaturereflux condenser
  3. customconnected to a calcium tube
  4. temperatureat reflux temperature over 1 day
  5. filtrationThe product mixture was filtered
  6. extractionextracted with EA (500 mL)
  7. dry with materialThe solution was dried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe product was purified by chromatography with hexane

Sources & evidence

ORD record
ord-e5abe67fc5a4499686e0ea0fa3c84b0b
Source dataset
uspto-grants-2007_06
Patent number
US07232822B2

Reaction notes

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