1,2-Dichloroethane → 1,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate

HRID 1366442Notes

Reaction equation

HRID 1366442 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].C(Cl)CCl.C[CH:21]=[CH:22][CH2:23][NH2:24]>CN(C1C=CN=CC=1)C>[CH2:23]([NH:24][C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:13][CH:14]=[CH2:15])=[O:12])[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 304472-Buten-1-amineHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acid

Product 1

HCID 866369391,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamateYield 28.4%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a stirred solution of (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentenoic acid (2.82 g, 13 mmol), DMAP (1.9 g, 16 mmol) and EDC (3.1 g, 16 mmol) was added N-methylallylamine (1.38 mL, 14 mmol). The reaction was stirred for 72 hours before being quenched by the addition of 1 M HCl (15 mL). The resulting biphasic mixture was separated and the aqueous phase was extracted once with DCM. The combined organics were dried over sodium sulfate and concentrated to yield 1,1-dimethylethyl {(1S)-1-[(2-propen-1-ylamino)carbonyl]-3-buten-1-yl}carbamate (0.94 g, 28%). LCMS: (M−tBut)+: 238.1.

Workup

  1. custombefore being quenched by the addition of 1 M HCl (15 mL)
  2. customThe resulting biphasic mixture was separated
  3. extractionthe aqueous phase was extracted once with DCM
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a2300e369d843569f06cdd4ef817e0f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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