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1,2-Dichloroethane → ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate

HRID 1855662
Notes
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Reaction equation

HRID 1855662 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH:36]1([C:42]2([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([N:45]1[CH2:46][CH2:47][C:42]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43][CH2:44]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7017908Boc-O-methyl-D-tyrosineHCID 18418945Ethyl 4-cyclohexyl-4-piperidinecarboxylate

Product 1

HCID 66987792
ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate
Yield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3.22 g (10.9 mmol) of (R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionic acid dissolved in 20 ml of DMF are added 2.29 g (12.0 mmol) of EDC, 1.62 g (12.0 mmol) of HOBt, 2.62 g (10.9 mmol) of ethyl 4-cyclohexylpiperidine-4-carboxylate and 4.6 ml (32.7 mmol) of triethylamine. After stirring for 2 hours 30 minutes, the reaction is stopped by adding aqueous 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and evaporated. The crude product obtained is chromatographed on silica gel (eluent: 7/3 heptane/EtOAc). 3.70 g of ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate in the form of a white powder are obtained in a yield of 66%.

Workup

  1. extractionthe organic products are extracted with dichloromethane
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product obtained
  6. customis chromatographed on silica gel (eluent: 7/3 heptane/EtOAc)

Sources & evidence

ORD record
ord-1eae674526664c31b2774f12c2c3362e
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962846B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes