Dichloromethane → HCID 178464388, compound

HRID 424481Notes

Reaction equation

HRID 424481 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][C:15]2[CH:19]=[C:20]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:21]=[CH:22][C:14]1=2)C(=O)OC(C)(C)C)[CH3:2].[OH-].[Na+].C(Cl)Cl>CO.Cl>[CH2:1]([NH:3][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][C:15]2[CH:19]=[C:20]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])[CH:21]=[CH:22][C:14]1=2)[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 178464390tert-Butyl ethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate

Product 1

HCID 178464388HCID 178464388, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Under positive argon pressure, an orange suspension of tert-butyl ethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)carbamate (4 g, 9.29 mmol) in MeOH (30 mL) and 1N HCl (30 mL) was refluxed for 1 hour. The mixture was then cooled to room temperature, transferred to an ice bath, and 1N NaOH (75 mL) was then added. The solution turned a milky green colour with a black suspension. The mixture was then treated with CH2Cl2 (50 mL) and stirred for half an hour. After this time, the mixture was transferred to a separatory funnel and the product was extracted into CH2Cl2 (2×50 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel using the following sequence of eluents: EtOAc; 1:99 (2M NH3 in MeOH):CH2Cl2; 2.5:97.5 (2M NH3 in MeOH):CH2Cl2; and 5:95 (2M NH3 in MeOH):CH2Cl2. A brown solid was obtained (2 g, 65.1%). 1H-NMR (CDCl3) δ 7.40-7.37 (m, 2H), 7.07-7.04 (m, 1H), 6.75-6.72 (m, 1H), 6.52-6.50 (m, 2H), 4.82 (brs, 2H), 4.24 (t, J=4.5 Hz, 2H), 3.39-3.31 (m, 4H), 2.86 (t, J=6.3 Hz, 2H), 2.71 (q, J=6.9 Hz, 2H), 1.13 (t, J=7.2 Hz, 3H); ESI-MS (m/z, %): 331 (MH+, 100), 260 (95); HPLC purity: 94.1% by area.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customtransferred to an ice bath
  3. customAfter this time, the mixture was transferred to a separatory funnel
  4. extractionthe product was extracted into CH2Cl2 (2×50 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customA brown solid was obtained (2 g, 65.1%)

Sources & evidence

ORD record
ord-71ec940a89814ddb98586a7a37d6ec07
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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