4-Methylmorpholine → HCID 178491874, compound

HRID 1486202Notes

Reaction equation

HRID 1486202 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[NH2:44][C@H:45]1[CH2:50][CH2:49][C@H:48]([CH2:51][C:52]([NH:54][C@H:55]([B:68]2[O:76][CH:75]3[C:70]([CH3:80])([CH:71]4[CH2:77][CH:73]([CH2:74]3)[C:72]4([CH3:79])[CH3:78])[O:69]2)[CH2:56][C:57]2[C:58]([O:66][CH3:67])=[C:59]([CH:63]=[CH:64][CH:65]=2)[C:60]([OH:62])=[O:61])=[O:53])[CH2:47][CH2:46]1>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:44][C@H:45]1[CH2:50][CH2:49][C@H:48]([CH2:51][C:52]([NH:54][C@H:55]([B:68]2[O:76][CH:75]3[C:70]([CH3:80])([CH:71]4[CH2:77][CH:73]([CH2:74]3)[C:72]4([CH3:79])[CH3:78])[O:69]2)[CH2:56][C:57]2[C:58]([O:66][CH3:67])=[C:59]([CH:63]=[CH:64][CH:65]=2)[C:60]([OH:62])=[O:61])=[O:53])[CH2:47][CH2:46]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178491870HCID 178491870, compound

Product 1

HCID 178491874HCID 178491874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-(tert-butoxycarbonylamino)acetic acid (175 mg) in a flask was added HATU (380 mg) and N-methyl morpholine (0.56 mL). After stirring at RT for 1 hr, this solution was added to 3-((2R)-2-(2-(trans-4-aminocyclohexyl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoic acid from Step 1 of Example 53 (110 mg) in DMF (3 mL). The resultant reaction mixture was stirred at RT overnight. Water was added to the reaction mixture and extracted with EtOAc. The organic phase was dried and concentrated in vacuo to afford the crude product which was used in next step without further purification.

Workup

  1. customThe resultant reaction mixture
  2. stirringwas stirred at RT overnight
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d9199c36eed4205b81b9a73d8817a86
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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