Ethyl Acetate → HCID 86599436, compound

HRID 1784956Notes

Reaction equation

HRID 1784956 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[C@@H:10]([C@H:31]([CH3:33])O)[NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.C(OC(=O)C)C>C1(C)C=CC=CC=1>[C:12]([N:11]1[C@@H:31]([CH3:33])[C@@H:10]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:34])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 131727364HCID 131727364, compound

Product 1

HCID 86599436HCID 86599436, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

N-Trityl-D-threonine benzyl ester (2.5 g, 5.5 mmol), TEA (2.8 ml, 20 mmol) were dissolved in 100 ml of dry toluene at −50° C. A solution of sulfuryl chloride (800 ul, 8 mmol) in toluene (20 ml) was added in 15 min. The reaction was allowed to warm up to r.t. Ethylacetate (100 ml) was added and this was washed with sat. NaCl, dried over Na2SO4. The product was crystallized in MeOH (10 ml) to give benzyl N-trityl-3(S)-methylaziridine-2(R)-carboylate. NMR (500 MHz, CDCl3) δ: 1.37 (d, 3H), 1.64 (m, 1H), 1.95 (d, 1H), 5.15(d, J=12 Hz, 1H), 5.28(d, J=12 Hz, 1H), 7.19˜7.28 (m, 12H), 7.33˜7.36 (m, 1H), 7.36˜7.39 (m, 3H), 7.51˜7.54 (m, 4H).

Workup

  1. washthis was washed with sat. NaCl
  2. dry with materialdried over Na2SO4
  3. customThe product was crystallized in MeOH (10 ml)

Sources & evidence

ORD record
ord-13d30fe1be93481c9a591cd17820f840
Source dataset
uspto-grants-2009_03
Patent number
US07504425B2

Reaction notes

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