Triphenylphosphine → tert-butyl (S)-1-((S)-5-((1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

HRID 1055461Notes

Reaction equation

HRID 1055461 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][N:14]([C@@H:22]([CH3:38])[C:23](=[O:37])[NH:24][C@H:25]1[CH2:31][O:30][C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[NH:27][C:26]1=[O:36])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[CH2:39]([N:41]1[C:49]2[C:44](=[C:45]([CH2:50]O)[CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42]1)[CH3:40].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:39]([N:41]1[C:49]2[C:44](=[C:45]([CH2:50][N:27]3[C:26](=[O:36])[C@@H:25]([NH:24][C:23](=[O:37])[C@@H:22]([N:14]([CH3:13])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[CH3:38])[CH2:31][O:30][C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]3=4)[CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42]1)[CH3:40]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 287420511H-Indole-4-methanol, 1-ethyl-2×HCID 72713380tert-Butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate

Product 1

HCID 131736363tert-butyl (S)-1-((S)-5-((1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamateYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD 40% w/w (359 mg, 376 μl, 826 μmol, Eq: 3) was added to a mixture of tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate (100 mg, 275 μmol, Eq: 1.00), (1-ethyl-1H-indol-4-yl)methanol (48.2 mg, 275 μmol, Eq: 1.00) and polymer-bound Ph3P (500 mg, 275 μmol, Eq: 1.00) in THF (10 mL). After 2.5 d., additional portions of (1-ethyl-1H-indol-4-yl)methanol (48.2 mg, 275 μmol, Eq: 1.00), polymer-bound Ph3P (1 eq) and DEAD (1 eq), were added. After 1 d, the mixture was filtered and the filter cake washed with MeOH and THF. The filtrate was concentrated and the residue was purified by preparative TLC to afford tert-butyl (S)-1-((S)-5-((l-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (73 mg, 51%).

Workup

  1. waitAfter 1 d
  2. filtrationthe mixture was filtered
  3. washthe filter cake washed with MeOH and THF
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-4b2ebe67868940d6a4f6a3b4ae86de5d
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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