Nitrogen → HCID 70980523, compound

HRID 2271342Notes

Reaction equation

HRID 2271342 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N#N.CCOC(/N=N/C(OCC)=O)=O.BrCCBr.[F:38][C:39]1[CH:40]=[C:41]([OH:49])[CH:42]=[C:43]([S:45]([CH3:48])(=[O:47])=[O:46])[CH:44]=1.[C:50]([NH:57][CH2:58][CH2:59]O)([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51]>C1COCC1.CCOC(C)=O.O>[F:38][C:39]1[CH:40]=[C:41]([CH:42]=[C:43]([S:45]([CH3:48])(=[O:46])=[O:47])[CH:44]=1)[O:49][CH2:59][CH2:58][NH:57][C:50](=[O:51])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54]

Participants

10

Reactant 6

HCID 947NitrogenHCID 78391,2-DibromoethaneHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 84662442HCID 84662442, compound

Product 1

HCID 70980523HCID 70980523, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of triphenylphosphine (1.9 g, 7.3 mmol) in dry THF (20 ml) was flushed with N2(g) and DEAD (3.1 ml, 6.9 mmol) was added drop-wise, 1.2-dibromoethane followed by 3-fluoro-5-methylsulfonyl-phenol (1.1 g, 6.1 mmol) and then boc-glycinol (1.0 ml, 6.1 mmol) in portions. The mixture was stirred at 70° C. for 20 h, cooled to room temperature and water and EtOAc was added. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with aqueous NaOH (3 M, 50 ml) and brine (75 ml), dried (Na2SO4) and evaporated. Purification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0) gave the title compound (1.4 g, 70%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic phase was washed with aqueous NaOH (3 M, 50 ml) and brine (75 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customPurification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0)

Sources & evidence

ORD record
ord-0e4f4e4a4e7f4d82a5a8aa1541f20587
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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