Sodium hydride → 2-(4-(2-(p-Methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

HRID 1264551Notes

Reaction equation

HRID 1264551 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.[H-].[Na+].[C:13]([O:17][C:18](=[O:56])[CH:19]([N:24]1[C:30](=[O:31])[CH:29]([NH:32][C:33](=[O:51])[CH:34](Br)[CH2:35][CH2:36][CH2:37][CH2:38][N:39]2[C:43](=[O:44])[C:42]3=[CH:45][CH:46]=[CH:47][CH:48]=[C:41]3[C:40]2=[O:49])[CH2:28][C:27]2[CH:52]=[CH:53][CH:54]=[CH:55][C:26]=2[CH2:25]1)[CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]([O:17][C:18](=[O:56])[CH:19]([N:24]1[C:30](=[O:31])[CH:29]([NH:32][C:33](=[O:51])[CH:34]([S:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:35][CH2:36][CH2:37][CH2:38][N:39]2[C:40](=[O:49])[C:41]3=[CH:48][CH:47]=[CH:46][CH:45]=[C:42]3[C:43]2=[O:44])[CH2:28][C:27]2[CH:52]=[CH:53][CH:54]=[CH:55][C:26]=2[CH2:25]1)[CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:15])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 538847672-(4-(2-Bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

Product 1

HCID 538676092-(4-(2-(p-Methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine p-methoxybenzylmercaptan (0.08 mL, 0.57 mmol) and-sodium hydride (17 mg, 60% oil dispersion, 0.42 mmol) in degassed dimethylformamide (3 mL). After 1 hour, tetra-n-butylammonium iodide (about 5 mg) and 2-(4-(2-bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester (0.27 mmol). After 20 hours, quench be the addition of a saturated aqueous ammonium chloride solution and dilute with water (about 5 mL). Extract with ethyl acetate (about 75 mL). Separate the layers and extract the orgainc layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. waitAfter 20 hours
  2. customquench
  3. additionthe addition of a saturated aqueous ammonium chloride solution
  4. additiondilute with water (about 5 mL)
  5. extractionExtract with ethyl acetate (about 75 mL)
  6. customSeparate the layers
  7. extractionextract the orgainc layer with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-9db7b64aea1c4681b0cb6c20704189e2
Source dataset
uspto-grants-2003_04
Patent number
US06544980B2

Reaction notes

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