m-Chloroperbenzoic acid → HCID 59815816, compound

HRID 429971Notes

Reaction equation

HRID 429971 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-27bab9b0d00f4c5691ce8fb034400fc6
Source dataset
uspto-grants-2001_11
Patent number
US06319946B1

Reaction notes

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