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

HRID 384732Notes

Reaction equation

HRID 384732 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-c4a88759875e48b1a64ebab542df09bd
Source dataset
uspto-grants-2013_02
Patent number
US08367732B2

Reaction notes

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