Hydrochloric Acid → HCID 59284760, compound

HRID 1778607Notes

Reaction equation

HRID 1778607 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:7]([OH:18])[CH2:6]1)=[O:4].N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(O)(C)C.[OH-].[Na+].C(Cl)(Cl)Cl>[C:11]([NH:10][C@@H:8]1[CH2:9][C@H:5]([C:3]([OH:2])=[O:4])[CH2:6][C@@H:7]1[O:18][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734526methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

Product 1

HCID 59284760HCID 59284760, compoundYield 87.1%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

Workup

  1. temperatureby heating at 40° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customwas quenched with H2O (3 mL)
  4. customThe organic layer was separated
  5. concentrationwas concentrated to dryness
  6. customto yield a residue, which
  7. temperatureThe reaction was cooled to 0° C.
  8. customthe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-14b9bac32bcf41eca302ca82c45fc7cd
Source dataset
uspto-grants-2016_02
Patent number
US09266919B2

Reaction notes

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