1,2-Dichloroethane → (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-5-(methoxy(methyl)amino)-5-oxopentanoate

HRID 405035Notes

Reaction equation

HRID 405035 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@@H:7]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:9][C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].Cl.CO[CH2:25][NH2:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CC[O:45][CH2:44]C1>>[CH3:25][N:26]([C:10](=[O:12])[CH2:9][CH2:8][C@@H:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[O:45][CH3:44]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 11244915(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-5-(methoxy(methyl)amino)-5-oxopentanoateYield 105.9%

Procedure

A mixture of (S)-5-tert-butoxy-4-(tert-butoxycarbonylamino)-5-oxopentanoic acid (3.03 g, 10 mmol) and methoxymethylamine HCl (1.17 g, 12 mmol) in HOBt (1.62 g, 12 mmol), EDC (2.3 g, 12 mmol) and NMM (3.3 mL, 30 mmol) was stirred at RT for 2 hr. The reaction was washed with 1N-HCl, NaHCO3 and sat. NaCl and dried over MgSO4. The solvent was removed to give 3.67 g of (S)-tert-butyl 3,11,11-trimethyl-4,9-dioxo-2,10-dioxa-3,8-diazadodecane-7-carboxylate, as a colorless oil. See, Syn. Lett. 2003, 10: 1411-1414.

Workup

  1. washThe reaction was washed with 1N-HCl, NaHCO3 and sat. NaCl
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-1251c927cc83478da05675a03011766f
Source dataset
uspto-grants-2014_06
Patent number
US08748649B2

Reaction notes

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