Trifluoroacetic acid → HCID 131724788, compound

HRID 984474Notes

Reaction equation

HRID 984474 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[O:21])=[CH:14][C:13]=3[N+:35]([O-:37])=[O:36])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:38]([OH:44])([C:40](F)(F)F)=[O:39].BrCC(OC(C)(C)C)=O>C(Cl)Cl.C(#N)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][N:25]([CH2:40][C:38]([OH:44])=[O:39])[CH2:24][CH2:23]4)=[O:21])=[CH:14][C:13]=3[N+:35]([O-:37])=[O:36])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 79177tert-Butyl bromoacetateHCID 131724789HCID 131724789, compound

Product 1

HCID 131724788HCID 131724788, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared by deprotection of the compound of Example 205 with TFA in CH2Cl2. The resultant free amine was treated with tert-butyl bromoacetate and TEA in acetonitrile at room temperature, and followed by deprotection with TFA in CH2Cl2, giving a light solid, mp 120° C. (dec.). 1H NMR (DMSO-d6, 300 MHz) δ 3.20-3.45 (m, 4H), 4.20 (s, 2H), 3.50-3.80 (m, 4H), 4.28-4.46 (m, 4H), 6.86 (d, J=8.5 Hz, 1H), 7.04 (m, J=8.0 Hz, 1H), 7.09 (dd, J=2.0 8.0 Hz, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.40 (d, J=15.5 Hz, 1H), 7.56 (d, J=15.0 Hz, 1H), 7.90 (dd, J=2.0, 8.5 Hz, 1H), 8.63 (m, 1H). MS (ESI) m/z 484 (M−H)+, 486 (M+H)+. Calcd. Anal for C23H21N3O7S.1.19CF3COOH.1.34H2O: 47.63; H, 4.11; N, 6.89. Found: C, 47.93; H, 4.51; N, 6.49.

Workup

  1. customgiving a light solid, mp 120° C. (dec.)

Sources & evidence

ORD record
ord-43fd9b4a1a23446f98c8548b6c5bb8b2
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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