Hydrochloric Acid → (S)-methyl 2-amino-6-(3-oxocyclobutanecarboxamido)hexanoate

HRID 1625696Notes

Reaction equation

HRID 1625696 reaction equation
C(OC([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)=[O:20])[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)=[O:20])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58481198(S)-methyl 2-(tert-butoxycarbonylamino)-6-(3-oxocyclobutanecarboxamido)hexanoate

Product 1

HCID 58481186(S)-methyl 2-amino-6-(3-oxocyclobutanecarboxamido)hexanoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-methyl 2-(tert-butoxycarbonylamino)-6-(3-oxocyclobutanecarboxamido)hexanoate (0.501 g) was treated with 20 mL 4M HCl in 1,4-dioxane at ambient temperature for 20 minutes and the solvent was removed under reduced pressure. The resulting viscous oil was taken up in 10 mL CH3CN, and seeded with small amount of crystals of the title compound prepared in a smaller scale. The resulting crystals were collected by vacuum filtration, washed with CH3CN, and dried under reduced pressure, affording (S)-methyl 2-amino-6-(3-oxocyclobutanecarboxamido)hexanoate (TU3205-016) as color less solid. MS (ESI+): calcd. 257.15. found 257.20 (MH+). H-NMR (400 MHz, DMSO-d6):1.267 (1H, m), 1.419 (3H, m), 1.753 (2H, m), 3.114 (7H, m), 3.752 (3H, m), 4.023 (1H, t, J=6.4 Hz), 8.169 (1H, t, J=5.5 Hz), 8.365 (3H, br.s). C-NMR (100 MHz, DMSO-d6): 21.499, 27.160, 28.390, 29.548, 38.067, 50.858, 51.721, 52.727, 169.949, 173.034, 205.586.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customprepared in a smaller scale
  3. filtrationThe resulting crystals were collected by vacuum filtration
  4. washwashed with CH3CN
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-65563207c14a44e6a9b5c7364878cf2a
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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