1,2-Dichloroethane → HCID 59302410, compound

HRID 2237369Notes

Reaction equation

HRID 2237369 reaction equation
C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:18]([O:22][C:23]([NH:25][C@@H:26]([C:32]([OH:34])=O)[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl.Cl.[CH3:40][O:41][C:42](=[O:50])[C@H:43]([CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47])[NH2:44]>ClCCl>[CH3:40][O:41][C:42](=[O:50])[C@H:43]([CH2:45][C:46]([CH3:48])([CH3:47])[CH3:49])[NH:44][C:32](=[O:34])[C@@H:26]([CH2:27][C:28]([CH3:29])([CH3:30])[CH3:31])[NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 7021114(R)-2-((tert-Butoxycarbonyl)amino)-4,4-dimethylpentanoic acidHCID 8661912979777-81-4

Product 1

HCID 59302410HCID 59302410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (3 equivalents, 39.4 g, 292 mmol), N-methylmorpholine (3 equivalents, 32.1 ml, 291.8 mmol), N-tert-butoxycarbonyl-3-tert-butyl-D-alanine (Example 6A, 1.0 equivalent, 97.3 mmol), EDC (2 equivalents, 37.3 g, 194.6 mmol) and again N-methylmorpholine (2 equivalents, 21.4 ml, 194.5 mmol) are added successively at −20° C. to a solution of 3-tert-butyl-L-alanine methyl ester hydrochloride (1.1 equivalents, 21 g, 107 mmol) in dichloromethane p.a. (1.4 l). The reaction mixture warms slowly (about 12 h) to RT, whereby complete conversion of the amine component is observed by means of HPLC. The reaction mixture is then washed with a saturated aqueous sodium hydrogen carbonate solution (300 ml), 5% aqueous citric acid (2×500 ml), a saturated aqueous sodium hydrogen carbonate solution (500 ml) and a saturated sodium chloride solution. The reaction mixture is dried over sodium sulfate and filtered. The mixture is concentrated to dryness in vacuo and then dried further under high vacuum. 36 g (96% of theory) of the title compound are obtained, which is reacted without further purification.

Workup

  1. customThe reaction mixture warms slowly (about 12 h)
  2. customto RT
  3. washThe reaction mixture is then washed with a saturated aqueous sodium hydrogen carbonate solution (300 ml), 5% aqueous citric acid (2×500 ml)
  4. dry with materialThe reaction mixture is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe mixture is concentrated to dryness in vacuo
  7. customdried further under high vacuum

Sources & evidence

ORD record
ord-4dd31210ea4b4e8d9b75f99dd50a2ae9
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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