Hydrochloric Acid → 7750-45-0

HRID 1741433Notes

Reaction equation

HRID 1741433 reaction equation
[C:1]([O:5][C:6](=[O:31])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OCC1C=CC=CC=1)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[ClH:32]>CCO>[ClH:32].[C:1]([O:5][C:6](=[O:31])[C@H:7]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10526923Nalpha-BOC-Nepsilon-CBZ-L-Lysine tert-Butyl Ester

Product 1

HCID 513584377750-45-0Yield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Nα -BOC-Nε -CBZ-L-lysine tert-butyl ester (2) (34.51 g, 79.15 mmol) was dissolved in a mixture of 300 ml absolute EtOH and 1 N HCl (88 ml). Prior to the introduction of H2 gas, 10% Pd--C (2.95 g) was added. After 7 hours, additional catalyst (1.0 g) was added. After 5 hours, the black suspension was filtered through a bed of Celite and washed with EtOH. The filtrate was concentrated and the residue dried under high vacuum to give the Nα -BOC-L-lysine tert-butyl ester as its hydrochloride salt (3) (26.59 g, 99%). 1H NMR (CD3OD) δ3.95 (dd, 1H, J=8.8, 5.0 Hz), 2.93 (t, 2H, J=7.7 Hz), 1.84-1.60 (m, 6H), 1.45 (s, 9H), 1.43 (s, 9H); 13C NMR (CD3OD) δ173.5, 158.2, 82.7, 80.5, 79.5, 55.5, 40.6, 32.1, 28.7, 28.3, 23.9. HRMS m/z calcd. for C15H31N2O4 303.2284, found 303.2272. [α]26D -10.1° (c=1.00, CH3OH).

Workup

  1. waitAfter 5 hours
  2. filtrationthe black suspension was filtered through a bed of Celite
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated
  5. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-ae9689ceafda4761a562d1c7a3047fe8
Source dataset
uspto-grants-1999_10
Patent number
US05973113

Reaction notes

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