Triethylamine → HCID 3625286, compound

HRID 1031758Notes

Reaction equation

HRID 1031758 reaction equation
C(OC(NC[C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12][CH2:11]1)=O)(C)(C)C.C([N:21](CC)CC)C.[C:26](Cl)(=O)[O:27][CH2:28][CH3:29].CNC(=O)[C@H](CC1C=CC=CC=1)NC([C@H:39]1[CH2:44][CH2:43][C@H](CNC(OC(C)(C)C)=O)[CH2:41][CH2:40]1)=O>O1CCCC1.CN(C)C=O>[O:27]([C:28]1[CH:29]=[C:15]([CH:10]=[CH:11][CH:12]=1)[CH2:14][CH:13]([C:16]([OH:18])=[O:17])[NH2:21])[C:26]1[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 178453624HCID 178453624, compoundHCID 178485750HCID 178485750, compound

Product 1

HCID 3625286HCID 3625286, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

On the other hand, trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarboxylic acid (1.62 g) was dissolved in dry tetrahydrofuran (50 ml) and N,N-dimethylformamide (20 ml), triethylamine (0.96 ml) was added, and a solution of ethyl chlorocarbonate (0.76 g) in dry tetrahydrofuran (2 ml) was added, followed by stirring for 30 minutes. To the solution, the previous hydrochloride (III) and triethylamine (2 ml) was added, and the mixture was stirred under room temperature for 3 hours. Ice-water (200 ml) was added to the reaction mixture, and the precipitated crystalline substance was collected by filtration, thoroughly washed with water, and dried to obtain 2.62 g of N-[trans-4-(t-butoxycarbonylaminomethyl)cyclohexylcarbonyl]-3-phenoxy-DL-phenylalanine 4-acetylanilide (IV). The NMR data did not contradict this result.

Workup

  1. stirringthe mixture was stirred under room temperature for 3 hours
  2. filtrationthe precipitated crystalline substance was collected by filtration
  3. washthoroughly washed with water
  4. customdried

Sources & evidence

ORD record
ord-30756c4412b04ee5bfcd755dc2977396
Source dataset
uspto-grants-1990_09
Patent number
US04954512

Reaction notes

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