Diisopropylethylamine → [(S)-1-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-2-((S)-3-methyl-morpholin-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 389640Notes

Reaction equation

HRID 389640 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]([C:17]1[S:18][C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][CH2:24][N:25](C(C)C)[CH:26]([CH3:28])[CH3:27].CN(C([O:39]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][NH:14][C:15]([C:17]1[S:18][C:19]([Cl:22])=[CH:20][CH:21]=1)=[O:16])[C:10]([N:25]1[CH2:24][CH2:23][O:39][CH2:27][C@@H:26]1[CH3:28])=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67155372(S)-2-tert-Butoxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-propionic acid

Product 1

HCID 67155152[(S)-1-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-2-((S)-3-methyl-morpholin-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 1 from step 1.1 was dissolved in 10 ml DCM and (3S)-methyl morpholine hydrochloride (276 mg, 2 mmol) was added followed by DIPEA (1.4 ml, 8 mmol) and HATU (761 mg, 2 mmol). After 1 h stirring at RT the reaction mixture was evaporated to dryness and the product was isolated by preparative HPLC.

Workup

  1. customwas evaporated to dryness
  2. customthe product was isolated by preparative HPLC

Sources & evidence

ORD record
ord-ac492dcbbbb345ee88ccb870378d2dc7
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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