Water → 5-Chloro-thiophene-2-carboxylic acid [(S)-2-amino-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide

HRID 389641Notes

Reaction equation

HRID 389641 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:18][NH:19][C:20]([C:22]1[S:23][C:24]([Cl:27])=[CH:25][CH:26]=1)=[O:21])[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]1[CH3:17])=[O:10])(C)(C)C.B(Br)(Br)Br.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[NH2:7][C@H:8]([C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]1[CH3:17])=[O:10])[CH2:18][NH:19][C:20]([C:22]1[S:23][C:24]([Cl:27])=[CH:25][CH:26]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67155152[(S)-1-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-2-((S)-3-methyl-morpholin-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 671552485-Chloro-thiophene-2-carboxylic acid [(S)-2-amino-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate 2 (306 mg, 0.708 mmol) from step 1.2 was dissolved in 3 ml of DCM, cooled to 0° C. and slowly treated with 1.42 ml (1.42 mmol) of a BBr3-solution (1M in DCM). After 2 h at 0° C. 7 ml sat. aq NaHCO3-solution and 3 ml H2O were added and the reaction was stirred for 15 min at RT. The organic layer was separated and the aqueous phase extracted with DCM. The combined organic layers were washed with H2O, dried with MgSO4, filtered and evaporated to dryness. 191 mg of crude product were obtained and used without further purification in step 1.8.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase extracted with DCM
  3. washThe combined organic layers were washed with H2O
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fb5900e8c79847559557dc550ffb1fab
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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