1,2-Dichloroethane → HCID 15384663, compound

HRID 2237370Notes

Reaction equation

HRID 2237370 reaction equation
C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:18]([O:22][C:23]([NH:25][C@@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl.Cl.[CH2:39]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH2:49])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl>[CH2:39]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:52])[CH3:53])[NH:49][C:31](=[O:33])[C@@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-Methylmorpholine2×HCID 757711-HydroxybenzotriazoleHCID 637604tert-Butoxycarbonyl-D-leucineHCID 12928659Benzyl L-leucinate--hydrogen chloride (1/1)

Product 1

HCID 15384663HCID 15384663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (4 equivalents, 540 mg, 4 mmol), N-methylmorpholine (3 equivalents, 3 mmol), N-tert-butoxycarbonyl-D-leucine (1.0 equivalent, 230 mg, 1 mmol; Bachem), EDC (2 equivalents, 380 mg, 2 mmol) and again N-methylmorpholine (2 equivalents, 2 mmol) are added successively at −10° C. to a solution of L-leucine benzyl ester hydrochloride (1.1 equivalents, 300 mg, 1.1 mmol; cf. T. Wakamiya, M. Kamata, S. Kusumoto, H. Kobayashi, Y. Sai, et al., Bull. Chem. Soc. Jpn., 1998, 71, 699-710) in dichloromethane p.a. (30 ml). 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 concentrated in vacuo, taken up in acetonitrile and purified by means of preparative HPLC (Method 13). 362 mg (80% of theory) of the title compound are obtained.

Workup

  1. customThe reaction mixture warms slowly (about 12 h)
  2. customto RT
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. custompurified by means of preparative HPLC (Method 13)

Sources & evidence

ORD record
ord-636ecc3c58c64a02967925d031894330
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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