1,2-Dichloroethane → HCID 67128600, compound

HRID 1189409Notes

Reaction equation

HRID 1189409 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:13][CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.Cl.[CH3:43][O:44][C:45](=[O:50])[C@H:46]([CH2:48][OH:49])[NH2:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH3:43][O:44][C:45](=[O:50])[CH:46]([NH:47][C:16](=[O:18])[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:4]2([CH3:3])[O:5][CH2:6][CH2:7][O:8]2)[CH:10]=1)[CH2:48][OH:49]

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 67128585HCID 67128585, compound

Product 1

HCID 67128600HCID 67128600, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid (2.20 g, 9.90 mmol) in CH2Cl2 (100 mL) was treated sequentially with DMAP (301 mg, 2.47 mmol), HOBT (1.61 g, 11.90 mmol), EDC (4.74 g, 24.75 mmol) and DIPEA (6.78 mL, 39.60 mmol). After stirring for 30 min at rt, serine methylester hydrochloride (1.62 g, 10.39 mmol) was added and the reaction mixture stirred overnight at rt. Water (100 mL) was added and the mixture was extracted twice with CH2Cl2 (100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (97:3 EA-MeOH) gave the title compound as a brown oil. TLC: rf (97:3 EA-MeOH)=0.45. LC-MS-conditions 02: tR=0.74 min; [M+H]+=324.41.

Workup

  1. stirringthe reaction mixture stirred overnight at rt
  2. extractionthe mixture was extracted twice with CH2Cl2 (100 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (97:3 EA-MeOH)

Sources & evidence

ORD record
ord-eab1cc22b6d3477bb93d1c8f410b3fbb
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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