Isobutyl chloroformate → HCID 20222343, compound

HRID 980239Notes

Reaction equation

HRID 980239 reaction equation
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC(OCC(C)C)=O.[NH2:30][C:31]1[C:39]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34]>C(Cl)Cl.CN1CCOCC1>[O:34]=[C:33]1[C:32]2[CH:36]=[CH:37][CH:38]=[C:39]([C:40]([F:41])([F:42])[F:43])[C:31]=2[N:30]=[C:19]([CH:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:21]1

Participants

6

Reactant 3

HCID 62365Isobutyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 20222343HCID 20222343, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 79724-MethylmorpholineSolvent2×

Procedure

Using the procedure of Step A of Example 7, a solution of 29.5 g of BOC-O-benzyl L-serine in 200 ml of methylene chloride, 27.5 ml of N-methyl-morpholine, 26.2 g of isobutyl chloroformate in methylene chloride and 20.5 g of 2-amino-3-trifluoromethyl benzoic acid in 200 ml of methylene chloride and 11 ml of N-methyl-morpholine were reacted for 16 hours. The mixture was extracted with methylene chloride and chromatography on silica gel (eluent: methylene chloride) yielded 18.5 g of 1,1-dimethylethyl N-[1-[4-oxo-8-trifluoromethyl-4H-3,1-benzoxazin-2-yl]-2-(phenylmethoxy)-ethyl]-carbamate melting at 98° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride and chromatography on silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-c34553c1cf464a86ab38f16a812aab2c
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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