tert-Butanol → HCID 67344737, compound

HRID 1669464Notes

Reaction equation

HRID 1669464 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH3:8][C:9]([OH:12])([CH3:11])[CH3:10].[C:13]([O:17][C:18]([N:20]([CH2:50][CH2:51][O:52][CH2:53][CH2:54][NH:55][CH3:56])[C@@H:21]1[CH2:28][N:27]2[C:29]3[CH:30]=[C:31]([C:42]([O:44][CH3:45])=[O:43])[CH:32]=[CH:33][C:34]=3[C:35]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[C:26]2[C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]=2[O:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN(CC)CC>C(Cl)Cl.CCOCC>[C:13]([O:17][C:18]([N:20]([CH2:50][CH2:51][O:52][CH2:53][CH2:54][N:55]([S:2]([NH:5][C:6]([O:12][C:9]([CH3:11])([CH3:10])[CH3:8])=[O:7])(=[O:4])=[O:3])[CH3:56])[C@@H:21]1[CH2:28][N:27]2[C:29]3[CH:30]=[C:31]([C:42]([O:44][CH3:45])=[O:43])[CH:32]=[CH:33][C:34]=3[C:35]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[C:26]2[C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]=2[O:23][CH2:22]1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 67345283HCID 67345283, compound

Product 1

HCID 67344737HCID 67344737, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonyl isocyanate (1.2 eq) was dissolved in dry DCM (0.2M) and 1.3 eq of a 2M solution of t-BuOH in ether was added at 0° C., after stirring for 1 h a 1 M solution of methyl (7R)-7-((tert-butoxycarbonyl){2-[2-(methylamino)ethoxy]ethyl}amino)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (1 eq) and NEt3 (3 eq) in dry DCM was added dropwise, and stirring was continued for 30 min at 0° C. and then at RT for 2 h. All volatiles were evaporated in vacuo and the residue was taken in EtOAc, washed with 1N HCl and brine, dried and concentrated; the crude material was purified by FC (Biotage, gradient of PE/EtOAc 1:1 to 1:3) to afford 40% of the title compound. (ES+) m/z 785 (M+H)+.

Workup

  1. additionwas added dropwise
  2. waitat RT for 2 h
  3. customAll volatiles were evaporated in vacuo
  4. washwashed with 1N HCl and brine
  5. customdried
  6. concentrationconcentrated
  7. customthe crude material was purified by FC (Biotage, gradient of PE/EtOAc 1:1 to 1:3)

Sources & evidence

ORD record
ord-4c8e33b971664131a95bde0d2b3c6349
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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