Benzaldehyde → HCID 101104055, compound

HRID 1067100

Reaction equation

HRID 1067100 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>O.CO>[CH2:19]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 101104055HCID 101104055, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Nδ-Boc-ornithine (7.0 g), 2M sodium hydroxide (20 ml), benzaldehyde (3.2 ml) and methanol (10 ml) was cooled to 0° C. and sodium borohydride (2.7 g) was added. After 1 hr at 0° C., the mixture was kept at 25° C. for 12 h. Water (100 ml) was added and the mixture extracted with ether (2×60 ml). The combined organic extract was washed with sat. sodium bicarbonate (ca. 150 ml) and water, and dried over anhydrous sodium sulfate. After concentration in vacuo, the desired product (4.5 g) was obtained as a white solid: 1H NMR (400 MHz, CD3OD) δ1.42 (s, 9H), 1.60 (m, 2H), 1.84 (m, 2H), 3.03 (m, 2H), 3.50 (t, J=7.4 Hz, 1H), 4.11 (d, J=11.9 Hz, 1H), 4.21 (d, J=11.9 Hz, 1H), 7.41 (m, 3H), and 7.49 (m, 2H).

Workup

  1. waitthe mixture was kept at 25° C. for 12 h
  2. extractionthe mixture extracted with ether (2×60 ml)
  3. extractionThe combined organic extract
  4. washwas washed with sat. sodium bicarbonate (ca. 150 ml) and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration in vacuo

Sources & evidence

ORD record
ord-4a3a99e99369426c9f31187f82c89fa7
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Linked notes

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