Isobutyl chloroformate → HCID 13578783, compound

HRID 980231Notes

Reaction equation

HRID 980231 reaction equation
[C:1]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC(OCC(C)C)=O.[NH2:31][C:32]1[C:40]([C:41]([F:44])([F:43])[F:42])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](O)=[O:35]>C(Cl)Cl.CN1CCOCC1.CC(O)=O>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:10][C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:20]2[O:22][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([F:42])([F:43])[F:44])[C:32]=3[N:31]=2)=[CH:12]1

Participants

7

Reactant 3

HCID 62365Isobutyl chloroformateHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 6045692-Amino-3-(trifluoromethyl)benzoic acid

Product 1

HCID 13578783HCID 13578783, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent3×HCID 79724-MethylmorpholineSolvent2×

Procedure

Using the procedure of Step A of Example 7, a solution of 22.8 g of BOC-L-Tryptophane in 150 ml of methylene chloride and 20.6 g of N-methyl-morpholine, 19.5 ml of isobutyl chloroformate in 75 ml of methylene chloride, 15.4 g of 2-amino-3-trifluoromethyl benzoic acid in 150 ml of methylene chloride and 8.3 ml of N-methyl-morpholine were reacted to obtain 20.7 g of 1,1-dimethylethyl N-[(S) 2-[1H-indol-3-yl]-1-[4-oxo-8-trifluoromethyl-4H-3,1-benzoxazin-2-yl]-ethyl-carbamate melting at 166° C. and having a specific rotation of [α]D =-52°±2.5° (c=0.4% in CH3COOH).

Workup

  1. customto obtain 20.7 g of 1,1-dimethylethyl N-[(S) 2-[1H-indol-3-yl]-1-[4-oxo-8-trifluoromethyl-4H-3,1-benzoxazin-2-yl]-ethyl-carbamate melting at 166° C.

Sources & evidence

ORD record
ord-376108a4f0f840d28f5783f29ea7f596
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

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