p-Bromobenzenesulfonyl chloride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

HRID 926010Notes

Reaction equation

HRID 926010 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@H:5]2[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]3[CH2:19][C@@:15]3([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]2[CH2:3]1.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:1][C@@H:2]2[CH2:27][CH2:26][C@H:5]3[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]4[CH2:19][C@@:15]4([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]3[CH2:3]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 69915043(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Product 1

HCID 88050650(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of compound 43 (0.13 mmol), TEA (0.39 mmol), and DMAP (0.009 mmol) in anhydrous DCM (0.3 mL) was added 4-bromobenzenesulfonyl chloride (0.17 mmol) in DCM (0.15 mL) dropwise. The reaction mixture was stirred at room temperature under nitrogen for 16 hrs. The crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3. The organics were concentrated to yield compound 44 as a yellow oil in a quantitative yield. MS (ESI, EI+): m/z=598 (MH+).

Workup

  1. washThe crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3
  2. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-72edad27e9154592ae93de74eedfed18
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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