Hydrochloric Acid → Benzyl 2(S)-tert-butoxycarbonylamino-5-nitro-4-oxopentanoate

HRID 269603

Reaction equation

HRID 269603 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:36]([CH3:39])([O-:38])=[O:37].CC(C)([O-])C.[K+].Cl>O1CCCC1>[C:19]([O:18][C:16]([NH:15][C@@H:10]([CH2:11][C:12](=[O:14])[CH2:39][N+:36]([O-:38])=[O:37])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:23])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 57481716Benzyl 2(S)-tert-butoxycarbonylamino-5-nitro-4-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution A of 10 g (30.9 mmol) of 2(S)-tert-butoxycarbonylaminosuccinic acid 1-benzyl ester and 5.27 g (32.5 mmol) of 1,1′-carbonyldiimidazole in 100 ml of tetrahydrofuran is stirred at RT for 5 h. 18.8 g (30.9 mmol) of nitromethane are added dropwise to a solution B of 3.2 g (34.2 mmol) of potassium tert-butoxide in 100 ml of tetrahydrofuran at 0° C. Solution B is stirred while warming to RT, and then solution A is added dropwise at RT. The resulting mixture is stirred at RT for 16 h and adjusted to pH 2 using 20% hydrochloric acid. The solvent is evaporated. The remaining crude product is taken up in ethyl acetate/water. After separation of the phases, the organic phase is extracted twice with water, dried over sodium sulfate and concentrated. 13 g (99% of theory) of product are obtained.

Workup

  1. customThe solvent is evaporated
  2. customAfter separation of the phases
  3. extractionthe organic phase is extracted twice with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custom13 g (99% of theory) of product are obtained

Sources & evidence

ORD record
ord-a333ce8cffdc4b388c26ccb6c89ee865
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Linked notes

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