m-Chloroperbenzoic acid → HCID 59815816, compound

HRID 1167268Notes

Reaction equation

HRID 1167268 reaction equation
[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:44])[NH:11][C@@H:12]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:13]([OH:36])[CH2:14][N:15]([S:24]([C:27]2[CH:35]=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[CH:28]=2)(=[O:26])=[O:25])[CH2:16][C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1.N1C=NN=N1.C(N(C(C)C)[P:54]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)(C)C.ClC1C=C(C=CC=1)C(OO)=[O:79]>C(Cl)Cl>[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:44])[NH:11][C@@H:12]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:13]([O:36][P:54]([O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)([O:63][CH2:64][C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:79])[CH2:14][N:15]([S:24]([C:27]2[CH:35]=[CH:34][C:30]3[O:31][CH2:32][O:33][C:29]=3[CH:28]=2)(=[O:25])=[O:26])[CH2:16][C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 196621Bis(benzyloxy)(diisopropylamino)phosphineHCID 480324[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[1,3-benzodioxol-5-ylsulfonyl-(4-cyano-2,2-dimethyl-butyl)amino]-1-benzyl-2-hydroxy-propyl]carbamateHCID 178418441HCID 178418441, compound

Product 1

HCID 59815816HCID 59815816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(4-cyano-2,2-dimethyl-butyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester (0.077 g, 0.12 mmol) and 1H-tetrazole (0.012 g, 0.17 mmol) in CH2Cl2 was treated with dibenzyl diisopropylphosphoramidite (0.050 ml, 0.015 mmol) and stirred at ambient temperature under argon. After 2 h 3-chloroperoxybenzoic acid (0.072 g, 0.30 mmol) was added and the reaction mixture stirred an additional 1 h. Solvent was removed in vacuo, the residue taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo to give desired product, which was used directly in the next step.

Workup

  1. stirringthe reaction mixture stirred an additional 1 h
  2. customSolvent was removed in vacuo
  3. washwashed with sat. aq. NaHCO3, and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-e14a31ef159243ff9c1a72201d1a75de
Source dataset
uspto-grants-2003_09
Patent number
US06617350B2

Reaction notes

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