Benzyl Nalpha-(Nalpha,Nepsilon-bis(t-butoxycarbonyl)-L-lysinoyl)-Nepsilon-(t-butoxycarbonyl)-L-lysine → (2S)-2-[[(2S)-2,6-Bis(tert-butoxycarbonylamino)hexanoyl]amino]-6-(tert-butoxycarbonylamino)hexanoic acid

HRID 1397118Notes

Reaction equation

HRID 1397118 reaction equation
C([N:8]([C:25](=[O:47])[C@H:26]([CH2:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:9]([C:22]([OH:24])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])C1C=CC=CC=1>CO.[Pd]>[C:31]([O:30][C:28]([NH:27][C@H:26]([C:25]([NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:47])[CH2:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:29])([CH3:32])([CH3:33])[CH3:34]

Participants

4

Reactant 1

HCID 86666531Benzyl Nalpha-(Nalpha,Nepsilon-bis(t-butoxycarbonyl)-L-lysinoyl)-Nepsilon-(t-butoxycarbonyl)-L-lysine

Product 1

HCID 86666530(2S)-2-[[(2S)-2,6-Bis(tert-butoxycarbonylamino)hexanoyl]amino]-6-(tert-butoxycarbonylamino)hexanoic acidYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A slurry of Pd—C (10% wt, 117 mg) in dry MeOH (2 mL) was added to a solution of benzyl ester 50 (1.17 g, 1.76 mmol) in dry MeOH (8.8 mL). The reaction vessel was flushed with hydrogen gas and stirred with a hydrogen balloon for 2 h 25 min. The reaction mixture was then filtered over celite to remove the catalyst. After rinsing the catalyst with small portions of MeOH, the combined filtrates were concentrated to dryness, providing acid 51 as a white solid (969 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 1.20-1.48 (m, 36H), 1.52-1.60 (m, 2H), 1.63-1.72 (m, 1H), 2.84-2.89 (m, 4H), 3.85-3.91 (m, 1H), 4.09-4.15 (m, 1H), 6.75 (bs, 2H), 6.80 (d, J=8.1 Hz, 1H), 7.88 (d, J=7.8 Hz, 1H).

Workup

  1. customThe reaction vessel was flushed with hydrogen gas
  2. filtrationThe reaction mixture was then filtered over celite
  3. customto remove the catalyst
  4. washAfter rinsing the catalyst with small portions of MeOH
  5. concentrationthe combined filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-d36597ab71b343ce923850f29733e43d
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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