Ethylamine → HCID 68605089, compound

HRID 218074Notes

Reaction equation

HRID 218074 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].ClC(OCC)=O.[OH:14][C@@H:15]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:16][CH2:17][C@@H:18]([O:27][CH2:28][CH:29]1[CH2:33][CH2:32][C:31](=[O:34])[NH:30]1)[C:19]1[S:23][C:22]([C:24]([OH:26])=O)=[CH:21][CH:20]=1.C(N)C>C(Cl)Cl>[CH2:1]([NH:3][C:24]([C:22]1[S:23][C:19]([C@H:18]([O:27][CH2:28][CH:29]2[CH2:33][CH2:32][C:31](=[O:34])[NH:30]2)[CH2:17][CH2:16][C@@H:15]([OH:14])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:20][CH:21]=1)=[O:26])[CH3:2]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 68608006HCID 68608006, compound

Product 1

HCID 68605089HCID 68605089, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (9 mL, 0.065 mmol) and ethyl chloroformate (4.5 mL, 0.47 mmol) were added sequentially to a solution of acid 6 (12 mg, 0.031 mmol) in CH2Cl2 (0.2 mL) at 0° C., After 1 h at 0° C., ethylamine (2.0 M in THF, 0.15 mL, 0.30 mmol) was added and the mixture was allowed to warm to room temperature. After 18 h at room temperature, the reaction was quenched with 1.0 N HCl (5 mL) and extracted with EtOAc (3×10 mL). The combined extracts were washed with brine (5 mL), then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on 4 g of silica gel (CH2Cl2→10% MeOH/CH2Cl2, gradient) afforded 7.7 mg (60%) of the title compound (8).

Workup

  1. customthe reaction was quenched with 1.0 N HCl (5 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined extracts were washed with brine (5 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude residue by flash column chromatography on 4 g of silica gel (CH2Cl2→10% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-654aaeb13dc041c0936198307009c37d
Source dataset
uspto-grants-2012_06
Patent number
US08198315B2

Reaction notes

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