1,2-Dichloroethane → HCID 88924275, compound

HRID 1507973Notes

Reaction equation

HRID 1507973 reaction equation
C(Cl)CCl.[C:5]([O:9][C:10]([NH:12][C@H:13]([CH3:20])[C@@H:14]([CH2:18][CH3:19])[C:15]([OH:17])=O)=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl.[NH2:22][C@@H:23]([CH2:28][OH:29])[C:24]([O:26][CH3:27])=[O:25].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[C:5]([O:9][C:10]([NH:12][C@H:13]([CH3:20])[C@@H:14]([CH2:18][CH3:19])[C:15]([NH:22][CH:23]([CH2:28][OH:29])[C:24]([O:26][CH3:27])=[O:25])=[O:17])=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 88924235HCID 88924235, compound

Product 1

HCID 88924275HCID 88924275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (2.01 g, 10.51 mmol) was added in one portion to a solution of (2R,3R)-3-((tert-butoxycarbonyl)amino)-2-ethylbutanoic acid (1.62 g, 7.00 mmol), (S)-methyl 2-amino-3-hydroxypropanoate hydrochloride (1.64 g, 10.51 mmol), HOBT (1.61 g, 10.51 mmol) and triethylamine (3.42 ml, 24.51 mmol) in anhydrous dichloromethane (28.0 ml). The reaction mixture was allowed to stir at rt under a nitrogen atmosphere overnight before evaporating in vacuo. The residue was then taken up in ethyl acetate (50 mL) and washed with water (50 mL). The organic was then dried (MgSO4) and evaporated in vacuo. The residue was treated with MeOH to precipitate title compound (1.71 g, 74%) which was used immediately in the next reaction. 1H NMR (400 MHz, CCl3D) δ 6.56 (d, J=6.6 Hz, 1H), 4.68 (dt, J=7.2, 3.5 Hz, 1H), 4.09-3.98 (m, 2H), 3.98-3.91 (m, 1H), 3.86 (br. s., 1H), 3.81 (s, 3H), 1.83-1.67 (m, 1H), 1.67-1.52 (m, 1H), 1.44 (s, 9H), 1.18 (d, J=6.8 Hz, 3H), 0.96 (t, J=7.5 Hz, 3H).

Workup

  1. custombefore evaporating in vacuo
  2. washwashed with water (50 mL)
  3. dry with materialThe organic was then dried (MgSO4)
  4. customevaporated in vacuo
  5. additionThe residue was treated with MeOH
  6. customto precipitate title compound (1.71 g, 74%) which
  7. customwas used immediately in the next reaction

Sources & evidence

ORD record
ord-183af93f538b4042bd558a064a451588
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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