HCID 7068955, compound → HCID 72546823, compound

HRID 2280086Notes

Reaction equation

HRID 2280086 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]1[CH2:13][CH2:14][C:15](=[O:16])[C:7]1=[C:6]2[C:17]1[CH:30]=[CH:29][C:20]([CH2:21][N:22]2[C:26](=[O:27])[CH:25]=[CH:24][C:23]2=[O:28])=[CH:19][CH:18]=1.[CH2:32]([O:34][C:35](=[O:47])[C@H:36]([CH2:45][SH:46])[NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH3:33]>C(Cl)Cl.CO>[C:41]([O:40][C:38]([NH:37][CH:36]([CH2:45][S:46][CH:25]1[CH2:24][C:23](=[O:28])[N:22]([CH2:21][C:20]2[CH:29]=[CH:30][C:17]([C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([N:2]([CH3:31])[CH3:1])[CH:4]=4)[CH:9]=[C:8]4[CH2:13][CH2:14][C:15](=[O:16])[C:7]=34)=[CH:18][CH:19]=2)[C:26]1=[O:27])[C:35]([O:34][CH2:32][CH3:33])=[O:47])=[O:39])([CH3:43])([CH3:44])[CH3:42]

Participants

4

Reactant 2

HCID 7068955HCID 7068955, compoundHCID 72546582HCID 72546582, compound

Product 1

HCID 72546823HCID 72546823, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

An oven-dried 25 mL one-necked round-bottomed flask equipped with a septum and a stir bar was charged with compound 17 (0.006 g, 0.015 mmol) in CH2Cl2/MeOH 1:1 (5 mL). N-Boc-L-cysteine ethyl ester (0.0036 g, 0.015 mmol) was added in one portion and the mixture mas stirred at rt for 10 min. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:1). The solution was then concentrated under reduced pressure and the reaction residue was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 1:1, to provide 0.006 g of the title compound as a 1:1 mixture of two inseparable diastereomers (d1 and d2) in a 60% yield.

Workup

  1. customAn oven-dried 25 mL one-necked round-bottomed flask equipped with a septum and a stir bar
  2. customThe consumption of the starting material
  3. concentrationThe solution was then concentrated under reduced pressure
  4. customthe reaction residue was purified by silica gel flash column chromatography
  5. washeluting with AcOEt/n-hexane 1:1

Sources & evidence

ORD record
ord-2e8c419047324f4fadf3632caef82be0
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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