Hydrochloric Acid → HCID 86761677, compound

HRID 1875358Notes

Reaction equation

HRID 1875358 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([NH:8][C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:10])[CH2:5][N:4]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[C:24](Cl)(=[O:26])[CH3:25].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[C:24]([NH:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([NH:8][C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:10])[CH2:5][N:4]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58748348HCID 58748348, compound

Product 1

HCID 86761677HCID 86761677, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

70.0 mg (0.2 mmol) tert. Butyl (2S,4R)-2-aminomethyl-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1-carboxylate are dissolved in 5 ml DCM and combined successively at −10° C. with 15.4 μl (0.2 mmol) acetyl chloride and 67 μl (0.4 mmol) DIPEA. The mixture is stirred for two hours at 0° C. Then it is made weakly acidic by the careful addition of dil. hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down i

Sources & evidence

ORD record
ord-852156edce2b4988b8a2f78857f1c2fa
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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