N-(tert-butoxycarbonyl)glycine → [[[(trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)amino]carbonyl]methyl]carbamic Acid 1,1-dimethylethyl Ester

HRID 16153Notes

Reaction equation

HRID 16153 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:30]=[CH:29][C:14]2[O:15][C:16]3[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=3[C@@H:18]3[C@H:23]([NH2:24])[CH2:22][CH2:21][CH2:20][N:19]3[C:13]=2[CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:55]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:56][C:57](O)=[O:58]>C(Cl)Cl>[CH3:66][C:63]([O:62][C:60](=[O:61])[NH:55][CH2:56][C:57]([NH:24][C@H:23]1[C@@H:18]2[N:19]([C:13]3[CH:12]=[C:11]([Cl:10])[CH:30]=[CH:29][C:14]=3[O:15][C:16]3[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=32)[CH2:20][CH2:21][CH2:22]1)=[O:58])([CH3:64])[CH3:65]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70883458trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 1

HCID 131728179[[[(trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)amino]carbonyl]methyl]carbamic Acid 1,1-dimethylethyl EsterYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA was added (pH=9) to trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (10 mg, 0.03 mmol) in 1 mL of CH2Cl2 with HATU (12.5 mg, 0.03 mmol) and Boc-Gly-OH (10.3 mg, 0.03 mmol). The resulting mixture was stirred for 3 h, washed with 5% aqueous sodium bicarbonate and H2O, dried (Na2SO4) and evaporated to give [[[(trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)amino]carbonyl]methyl]carbamic Acid 1,1-dimethylethyl Ester (14.3 mg, 100%). Data: (m/z)=405 (M+H)+.

Workup

  1. washwashed with 5% aqueous sodium bicarbonate and H2O
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-1224c8fed8e1451682bdaa4303075bb8
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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