Triethylamine → HCID 22556071, compound

HRID 1274538Notes

Reaction equation

HRID 1274538 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.Cl.[CH3:36][O:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][NH:47][CH2:48][C:49]2[CH:58]=[CH:57][C:52]([C:53]([O:55][CH3:56])=[O:54])=[C:51]([O:59][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[CH:50]=2)=[CH:42][C:41]=1[O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:39]>Cl.CN(C)C=O>[CH3:36][O:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][N:47]([CH2:48][C:49]2[CH:58]=[CH:57][C:52]([C:53]([O:55][CH3:56])=[O:54])=[C:51]([O:59][CH2:60][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[CH:50]=2)[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])=[CH:42][C:41]=1[O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 22556092HCID 22556092, compound

Product 1

HCID 22556071HCID 22556071, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved N-Cbz-6-aminohexanoic acid (784 mg, 2.96 mmole) into 10 mL of N,N-dimethylformamide and cooled to 0° C. Added triethylamine (1.65 mL, 11.8 mmole), stirred for 10 minutes, then added isobutylchloroformate (385 uL, 2.68 mmole). Stirred for 45 minutes and then added the crude methyl 4-[({[4-(methoxycarbonyl)-3-(phenylmethoxy)phenyl]methyl}-amino)-methyl]-2-(phenylmethoxy)benzoate hydrochloride from the step above (830 mg, 1.48 mmole). Let warm to room temperature and stirred for 3 hours. Diluted the reaction mixture with 1 N HCl and extracted with ethyl acetate. Dried the ethyl acetate layers with brine and anhydrous magnesium sulfate. Filtered, removed solvents in vacuo, and chromatographed on silica gel. Collected 870 mg (76% yield) of product.

Workup

  1. temperatureLet warm to room temperature
  2. stirringstirred for 3 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialDried the ethyl acetate layers with brine and anhydrous magnesium sulfate
  5. filtrationFiltered
  6. customremoved solvents in vacuo
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2c58b837e004498a9f533931e4285a2a
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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