1,2-Dichloroethane → 3-Hydroxy-2-{2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetylamino}-propionic acid methyl ester

HRID 1189399Notes

Reaction equation

HRID 1189399 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][C:15]([OH:17])=O)=[CH:11][CH:10]=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.[CH3:42][O:43][C:44](=[O:49])[C@H:45]([CH2:47][OH:48])[NH2:46].[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:42][O:43][C:44](=[O:49])[CH:45]([NH:46][C:15](=[O:17])[CH2:14][C:12]1[S:13][C:9]([C:4]2([CH3:3])[O:5][CH2:6][CH2:7][O:8]2)=[CH:10][CH:11]=1)[CH2:47][OH:48]

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 67128426HCID 67128426, compound

Product 1

HCID 671285993-Hydroxy-2-{2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetylamino}-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetic acid (1.25 g, 5.48 mmol) in CH2Cl2 (20 mL) was treated sequentially with DMAP (135 mg, 1.10 mmol), HOBT (1.07 g, 6.80 mmol), EDC (2.68 g, 13.69 mmol) and DIPEA (3.85 mL, 21.9 mmol). After stirring for 1 h at rt, serine methylester hydrochloride (913 g, 5.75 mmol was added and the reaction mixture stirred for 1 h at rt. Sat. aq. NH4Cl was added and the mixture was extracted twice with CH2Cl2. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1000:25:2 CH2Cl2-MeOH—NH4OH) gave the title compound as an orange oil. TLC: rf (EA)=0.3. LC-MS-conditions 01: tR=0.68 min; [M+H]+=329.94.

Workup

  1. stirringthe reaction mixture stirred for 1 h at rt
  2. extractionthe mixture was extracted twice with CH2Cl2
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (1000:25:2 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-9e94483887c146b2aabaab4d6acc05ae
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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