Hydrochloric Acid → HCID 131730789, compound

HRID 1887400Notes

Reaction equation

HRID 1887400 reaction equation
[ClH:1].O1CCOCC1.[OH:8][C@@H:9]1[C@H:13]2[N:14]([C:18](=[O:32])[C@@H:19]([NH:24]C(=O)OC(C)(C)C)[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][C@@H:16]([CH3:17])[C@H:12]2[O:11][CH2:10]1>>[ClH:1].[NH2:24][C@@H:19]([C:20]([CH3:21])([CH3:23])[CH3:22])[C:18]([N:14]1[CH2:15][C@@H:16]([CH3:17])[C@H:12]2[O:11][CH2:10][C@H:9]([OH:8])[C@@H:13]12)=[O:32]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86652253HCID 86652253, compound

Product 1

HCID 131730789HCID 131730789, compound

Procedure

A solution of 4N HCl in 1,4-dioxan (20 mL, 80 mmol) was added to tert-butyl (S)-1-((3R,3aR,6R,6aR)-3-hydroxy-6-methyldihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (1.43 g, assuming 4.0 mmol). The solution was stirred for 90 minutes then the solvents were removed in vacuo and the residue azeotroped with TBME (3×25 mL) to leave (S)-2-amino-1-((3R,3aR,6R,6aR)-3-hydroxy-6-methyldihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-3,3-dimethylbutan-1-one, hydrochloride as a purple crystalline solid which was used without further purification. HPLC-MS 257.2 [M+H]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue azeotroped with TBME (3×25 mL)

Sources & evidence

ORD record
ord-a6d23b800f89459c8678011b68b7da91
Source dataset
uspto-grants-2013_08
Patent number
US08501744B2

Reaction notes

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