Chloroacetyl chloride → HCID 131729386, compound

HRID 420312Notes

Reaction equation

HRID 420312 reaction equation
[NH2:1][C:2]1[C:31]([O:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:38].[Cl:39][CH2:40][C:41](Cl)=[O:42]>C1(C)C=CC=CC=1>[C:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:12]1[C@@H:11]2[C@H:15]([C@H:7]([CH2:6][C:5]3[CH:30]=[C:31]([O:32][CH2:33][C:34]([F:36])([F:37])[F:35])[C:2]([NH:1][C:41](=[O:42])[CH2:40][Cl:39])=[C:3]([F:38])[CH:4]=3)[CH2:8][S:9](=[O:29])(=[O:28])[CH2:10]2)[O:14][C:13]1=[O:16])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 66649644HCID 66649644, compound

Product 1

HCID 131729386HCID 131729386, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared in analogous manner as described for example 8p) from (3aR,7S,7aS)-7-[4-amino-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (400 mg, 0.716 mmol) and chloroacetylchloride (324 mg, 2.86 mmol) to yield a white foam: TLC Rf=0.40 (toluene-ETA 85:15); ESIMS [M+NH4]+=652, 654, [M−H]−=633, 635; UPLC RtD=1.861 min; 1H NMR (600 MHz, DMSO-d6): δ 9.64 (s, 1H, NH), 7.41 (s, 1H), 7.33 (d, 1H), 7.28 (t, 1H), 7.13 (d, 1H), 6.91 (s, 1H), 6.88 (d, 1H), 4.74 (q, 2H), 4.43 (d, 1H), 4.25-4.18 (m, 4H), 3.78 (d, 1H), 3.65 (t, 1H), 3.50 (t, 1H), 3.17 (t, 1H), 2.99 (m, 2H), 2.56 (m, 2H), 1.25 (s, 9H).

Workup

  1. customto yield a white foam
  2. customUPLC RtD=1.861 min

Sources & evidence

ORD record
ord-8f87e8c24ef94e74b683786f56286aa6
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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