Water → HCID 9966032, compound

HRID 993465Notes

Reaction equation

HRID 993465 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:21])[CH:8]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]=1[O:11][CH3:12])=[O:5])[CH3:2].C(OC(NC1C(O)=C(C(OCC)=O)N(C)C=1)=O)C1C=CC=CC=1.[OH-].[Na+].O>C(O)C>[C:17]([O:16][C:14]([NH:13][C:9]1[C:10]([O:11][CH3:12])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]([CH3:21])[CH:8]=1)=[O:15])([CH3:19])([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70158169HCID 70158169, compound

Product 1

HCID 9966032HCID 9966032, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate Ethyl 4-[(tert-butoxycarbonyl)amino]-3-methoxy-1-methylpyrrole-2-carboxylate (9.0 g, 30.2 mmol) was dissolved in 30 mL ethanol. NaOH (30 ml, 1 M, aq) was added and the solution stirred for 4 days. Water (200 ml) was added and ethanol removed in vacuo. The solution was extracted with diethyl ether, aqueous layer acidified to pH=2-3, and extracted again with diethyl ether. Organic layers were dried over MgSO4, and solvent removed in vacuo to give a white solid (6.0 g, 20.5 mmol, 87% based on recovered SM) 1H NMR (DMSO-d6) δ 12.14 (s, 1H), 8.37 (s, 1H), 6.98 (s, 1H), 3.69 (s, 3H), 3.66 (s, 3H), 1.42 (s, 9H); MS m/e 293.112 (M+H 293.104 calcd. for C12H18N2O5).

Workup

  1. customethanol removed in vacuo
  2. extractionThe solution was extracted with diethyl ether, aqueous layer
  3. extractionextracted again with diethyl ether
  4. dry with materialOrganic layers were dried over MgSO4, and solvent
  5. customremoved in vacuo
  6. customto give
  7. customa white solid (6.0 g, 20.5 mmol, 87% based on recovered SM) 1H NMR (DMSO-d6) δ 12.14 (s, 1H), 8.37 (s, 1H), 6.98 (s, 1H), 3.69 (s, 3H), 3.66 (s, 3H), 1.42 (s, 9H)

Sources & evidence

ORD record
ord-747177f119be43efa37477ca019c4f00
Source dataset
uspto-grants-2002_10
Patent number
US06472537B1

Reaction notes

Loading…