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Methyl bromoacetate → (3-tert-Butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)acetic Acid Methyl Ester

HRID 502325
Notes
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Reaction equation

HRID 502325 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OC(NC1C(=O)NC2C=CC=CC=2NC1)=O)(C)(C)C.BrCC(OC)=O>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[CH:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 60984Methyl bromoacetateHCID 2733832Lithium hexamethyldisilazaneHCID 154908313-Tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-oneHCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Product 1

HCID 54305290
(3-tert-Butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)acetic Acid Methyl Ester
Yield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(3(S)-tert-Butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)acetic acid methyl ester (103). A 1.0 M solution of lithium bis(trimethylsilyl)amide (3.4 ml, 3.4 mmol) in THF was added dropwise to a −78° C. solution of 3-tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one (0.94 g, 3.38 mmol) in 20 ml of anhydrous tetrahydrofuran and stirred for 30 minutes. Methyl bromoacetate (0.44 ml, 4 mmol) was added dropwise to the reaction mixture then warmed to room temperature. The reaction was diluted with 100 ml of ethyl acetate and washed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine. The combined organics were dried over anhydrous sodium sulfate, filtered, and evaporated to afford a gum that was purified by flash chromatography eluting with 3:7 EtOAc/Hex. to give 0.98 g (83%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.15-7.07 (2H, m), 6.98-6.94 (1H, m), 6.88-6.84 (1H, d), 5.62-5.55 (1H, d), 4.71-4.65 (1H, d), 4.65-4.6 (1H, m), 4.33-4.27 (1H, d), 3.96-3.90 (1H, m), 3.78 (3H, s), 3.44-3.37 (1H, m), 1.4 (9H, s).

Workup

  1. washwashed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a gum that
  6. customwas purified by flash chromatography
  7. washeluting with 3:7 EtOAc/Hex

Sources & evidence

ORD record
ord-57399eb203344c3f8dac98cef634a149
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772366B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes