N-(tert-butoxycarbonyl)glycine → HCID 67040880, compound

HRID 605153Notes

Reaction equation

HRID 605153 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)=[O:11])=[CH:8][C:7]=1[NH:22][C:23]1[C:24]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[N:29][C:25]=2[N:26]=[CH:27][N:28]=1.[C:39]([O:43][C:44]([NH:46][CH2:47][C:48](O)=[O:49])=[O:45])([CH3:42])([CH3:41])[CH3:40].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[C:39]([O:43][C:44](=[O:45])[NH:46][CH2:47][C:48](=[O:49])[NH:1][C:2]1[CH:38]=[CH:37][CH:36]=[C:4]([O:5][C:6]2[CH:21]=[CH:20][C:9]([C:10](=[O:11])[NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[CH:8][C:7]=2[NH:22][C:23]2[C:24]3[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[N:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH:3]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

8

Reactant 5

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67040737HCID 67040737, compound

Product 1

HCID 67040880HCID 67040880, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 109 (0.068 g, 0.1 mmol), tert-Butoxycarbonylamino-acetic acid (0.023 g, 0.13 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.025 g, 0.13 mmol), 1-Hydroxybenzotriazole hydrate (0.015 g, 0.11 mmol) and N,N-diisopropylethylamine (0.029 g, 0.22 mmol) in N,N-dimethylformamide (2 mL) was stirred for 16 hours, poured into water and extracted with ethyl acetate (3×15 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under vacuum to provide a residue which was purified by chromatography on silica eluting with 96:4 dichloromethane/methanol to provide the title compound (50 mg, 69%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.31 (d, J=6.62 Hz, 6 H), 1.38 (s, 9 H), 3.13-3.27 (m, 1 H), 3.68 (d, J=5.88 Hz, 2 H), 6.63-6.71 (m, 1 H), 7.04 (t, J=6.43 Hz, 1 H), 7.08 (d, J=8.46 Hz, 1 H), 7.24 (d, J=4.78 Hz, 2 H), 7.26-7.37 (m, 2 H), 7.49 (s, 1 H), 7.58 (d, J=8.46 Hz, 1 H), 7.72-7.79 (m, 1 H), 7.92 (dd, J=8.64, 2.02 Hz, 1 H), 8.11 (s, 1 H), 8.19 (d, J=1.47 Hz, 1), 8.59 (s, 1 H), 8.76 (d, J=8.46 Hz, 1 H), 10.00 (s, 1 H), 10.05 (s, 1 H), 10.39 (s, 1 H).

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto provide a residue which
  6. customwas purified by chromatography on silica eluting with 96:4 dichloromethane/methanol

Sources & evidence

ORD record
ord-e671f2eb22254d14bb191b14189bff41
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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